N-hydrocarbyl Morpholines Patents (Class 544/178)
  • Patent number: 5089614
    Abstract: An essentially single stage reaction has been discovered in which a disubstituted ethanolamine, that is, a 2,2'-substituted-2-aminoethanol, may be reacted with a haloform and a carbonyl containing compound selected from the group consisting of monoketones and benzaldehyde, in the presence of an alkali metal hydroxide, and optionally in the presence of a phase transfer catalyst, to produce an alkali metal hydroxyethylaminoacetate ("HEAA") which has N-adjacent C atoms on which there are a total of at least three substituents (hence "polysubstituted"), and one or both pairs of substituents on each N-adjacent C atom may be cyclized. The HEAA may be cyclized by the action of a mineral acid to produce a 2-morpholone hydrochloride which is characterized by having a total of at least three substituents on the N-adjacent C atoms of the ring. The 2-morpholone so produced may be reduced to a polysubstituted aminodiol.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: February 18, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5082840
    Abstract: A method for increasing the weight gain and/or improving the feed utilization efficiency and/or increasing the lean body mass and/or decreasing birth mortality rate and increasing post-natal survival rate of livestock comprises the administration to livestock of an effective, non-toxic amount of a compound of formula (I), or a veterinarily acceptable acid addition salt thereof: ##STR1## wherein R.sup.1 is phenyl (C.sub.1-6) alkyl or optionally substituted C.sub.1-6 alkyl, andW is optionally substituted phenyl, a heterocyclyl group, or phenoxymethyl optionally substituted on the phenyl group. Certain compounds of formula (I) are novel.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: January 21, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Jonathan R. Arch, Norman H. Rogers
  • Patent number: 5022916
    Abstract: The present invention relates to compounds of the formula (I) or salts thereof ##STR1## where R.sup.1, R.sup.2 or H, are saturated or unsaturated (substituted) aliphatic radicals or (substituted) phenyl, or R.sup.1 and R.sup.2 together with the N atom by which they are linked are a heterocyclic ring of the formula ##STR2## a indices independently of one another being an integer from 1 to 3, R.sup.3 is H, a saturated or unsaturated (substituted) aliphatic radical or a (substituted) phenyl, benzyl or phenethyl radical, or R.sup.2 and R.sup.3 together are an alkylene chain,R.sup.4 is H, a saturated or unsaturated aliphatic radical or alkoxy, andR.sup.5 is a (substituted) pyrimidinyl, triazinyl, triazolyl or bicyclic, nitrogen-containing heterocyclic radical, which have valuable herbicidal or plant growth-regulating properties.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: June 11, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Lothar Willms, Klaus Bauer, Hermann Bieringer, Helmut Burstell
  • Patent number: 4910304
    Abstract: N-substituted cyclic amines of the general formula I ##STR1## where A is an alkylene group or a --(CH.sub.2).sub.n --[--O--(CH.sub.2).sub.m ].sub.r group which may be monosubstituted or polysubstituted by radicals R without the radicals R in a defined compound having to be identical, R is alkyl, alkoxyalkyl, unsubstituted or alkyl-substituted or alkoxy-substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, n and m independently of one another are each from 2 to 8 and r is from 1 to 3, the --(CH.sub.2).sub.n --[O--(CH.sub.2).sub.m ].sub.r group consisting of from 5 to 12 members, are prepared by reacting a primary amine of the general formula IIR--NH.sub.
    Type: Grant
    Filed: March 31, 1989
    Date of Patent: March 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Fischer, Herbert Mueller, Dieter Voges
  • Patent number: 4785006
    Abstract: The invention provides fungicidal compositions comprising as an active ingredient a compound having the general formula (I): ##STR1## or a stereoisomer thereof wherein X and Y are hydrogen, alkyl, or alkoxy, provided that when one of X and Y is hydrogen the other is not --C(CH.sub.3).sub.2 R, where R is hydrogen, methyl or ethyl; Z is carbonyl, or a derivative thereof, or is --CR.sup.3 R.sup.4 -- or --CR.sup.3 OR.sup.4 -- in which R.sup.3 and R.sup.4 are hydrogen or C.sub.1-4 alkyl; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen or C.sub.1-4 alkyl, or R.sup.1 and R.sup.2 together with the adjacent N-atom constitute an optionally substituted heterocyclic ring; and n is 0 or 1.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: November 15, 1988
    Inventors: Paul A. Worthington, Brian K. Snell, Paul DeFraine, Vivienne M. Anthony
  • Patent number: 4785100
    Abstract: A process is provided for the production of N-substituted morpholines and piperidines of the formula ##STR1## comprising the steps of (a) reacting a methallylbenzene of the formulas ##STR2## wherein R.sub.1 is H or a straight or branched chained C.sub.1 -C.sub.4 alkyl group, alone or in admixture with a corresponding isobutenylbenzene of the formula ##STR3## wherein R.sub.1 is as defined above, with hydrogen bromide in the presence of a peroxide to yield, respectively, the corresponding bromine compound of the formula ##STR4## wherein R.sub.1 is as defined above, alone or in admixture with a bromine compound of the formula ##STR5## wherein R.sub.1 is as defined above and wherein the bromine atom is in the secondary or tertiary position, and(b) reacting the resultant bromine compound of formula IV, alone or in admixture with the corresponding bromine compound of Formula V, with a compound of the formula ##STR6## wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: November 15, 1988
    Assignee: Huels Aktiengesellshaft
    Inventor: Manfred Kaufhold
  • Patent number: 4777176
    Abstract: This invention provides fungicidal compositions comprising as an active ingredient a compound having the general formula (I): ##STR1## or a stereoisomer thereof, wherein one of X and Y represents hydrogen and the other represents the group ##STR2## in which R is hydrogen, methyl or ethyl; Z represents hydrogen or an alkyl group containing from one to four carbon atoms; R.sup.1 and R.sup.2, which may be the same or different, represent hydrogen or an alkyl group containing one to four carbon atoms, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent an optionally-substituted heterocyclic ring; and n is 0 or 1.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: October 11, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul A. Worthington, Brian K. Snell, Paul DeFraine, Vivienne M. Anthony
  • Patent number: 4727151
    Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein N represents a tertiary aliphatic amine; wherein N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.
    Type: Grant
    Filed: November 22, 1978
    Date of Patent: February 23, 1988
    Assignee: INTERx Research Corporation
    Inventor: Nicolae S. Bodor
  • Patent number: 4721786
    Abstract: Fungicidally active novel .beta.-naphthylalkylamines of the formula ##STR1## in which Ar represents optionally substituted .beta.-naphthyl andR.sup.1 and R.sup.2, which can be identical or different, represent alkyl or alkenyl orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, represent an optionally substituted saturated heterocyclic radical, which can contain further hetero-atoms,or plant-tolerated acid addition salts thereof.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: January 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Weissmuller, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4714699
    Abstract: The present invention relates to new 2-tolylmorpholine derivatives, namely, more precisely,(a) 2-p-tolyl-4-isopropylmorpholine and its addition salts,(b) 2-m-tolyl-4-methylmorpholine and its addition salts,(c) 2-p-tolyl-4-methylmorpholine and its addition salts,(d) 2-o-tolyl-4-tert.-butylmorpholine and its addition salts,(e) 2-p-tolyl-4-tert.-butylmorpholine and its addition salts, and(f) 2-(m-trifluoromethylphenyl)-2-hydroxy-4-ethylmorpholine and its addition salts.These new derivatives are useful in therapy, especially as agents active on the CNS.
    Type: Grant
    Filed: March 18, 1987
    Date of Patent: December 22, 1987
    Assignee: Societe Anonyme Dite: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4705553
    Abstract: Novel phenylalkylcycloamines, their preparation, agents containing these compounds, and methods for regulating plant growth.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: November 10, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Walter Himmele, Heinz Eckhardt, Hansgeorg Ernst, Wilhelm Rademacher, Johann Jung
  • Patent number: 4695631
    Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: September 22, 1987
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
  • Patent number: 4670557
    Abstract: This invention relates to the reaction of aliphatic epoxides and primary amines to form hydroxymorpholines or morpholines by a process comprising reacting said epoxide and primary amine in the presence of a ruthenium-containing compound plus a tertiary phosphine.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: June 2, 1987
    Assignee: Texaco Inc.
    Inventor: Wei-Yang Su
  • Patent number: 4647664
    Abstract: N-alkylmorpholines are prepared by passing a reaction mixture over a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages, the reaction mixture being composed of a C.sub.1 -C.sub.4 primary alkyl alcohol and a feedstock selected from the class consisting of morpholine, diethanolamine and bis-aminoethylether.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Steven H. Vanderpool, Robert L. Zimmerman
  • Patent number: 4606755
    Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: August 19, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Morris P. Rorer
  • Patent number: 4602088
    Abstract: A method for the preparation of enamines wherein a conjugated diene is reacted with a secondary amine, carbon monoxide and hydrogen (synthesis gas) in solvent solution in the presence of a rhodium catalyst. In accordance with the preferred embodiment, butadiene is reacted with a dialkylamine and synthesis gas in an organic solvent in the presence of a rhodium catalyst to provide the corresponding 1,3-pentadienyl dialkylamine in good yield and with good selectivity.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4582904
    Abstract: Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: April 15, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: James E. Wells, Victoria Eskinazi
  • Patent number: 4568772
    Abstract: This invention discloses a novel process for producing p-t-butyl-.alpha.-methyldihydrocinnamaldehyde which comprises converting the .alpha.-methyldihydrocinnamaldehyde to an enamine, oxazolidine or a Schiff's base, reacting said derivative with a tertiary butyl cation, and then removing the protective group.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: February 4, 1986
    Assignee: Givaudan Corporation
    Inventors: Albert Gabbai, Karl-Fred De Polo
  • Patent number: 4551532
    Abstract: New ethylene glycol derivatives, inclusive of salts thereof, which have the formula: ##STR1## wherein n is an integer of 1 to 15; R.sup.1 is an aliphatic hydrocarbon group containing 6 to 26 carbon atoms; R.sup.2, R.sup.3 and R.sup.4 are independently H or lower alkyl, or ##STR2## represents a cyclic ammonio group, exhibit inhibitory activity to multiplication of tumor cells and antimicrobial activity.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: November 5, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Motoo Hozumi, Hiroaki Nomura, Yoshio Yoshioka
  • Patent number: 4543411
    Abstract: Secondary and tertiary amines are selectively prepared by a process comprising reacting an olefin, a nitrogen-containing compound and synthesis gas in the presence of a catalyst system comprising a ruthenium-containing compound mixed with a quaternary onium salt, optionally in the presence of a solvent, heating the resultant mixture to a temperature of at least 100.degree. C. and a pressure of at least 100 psi until there is substantial formation of the desired tertiary amine and separating the desired amine by a phase separation technique.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: September 24, 1985
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, David C. Alexander
  • Patent number: 4537713
    Abstract: The invention concerns a process for the reduction of groups containing unsaturated C,C--, C,N--,N,N--,N,O-- bonds, especially of NO.sub.2 --,NO--,NOH--,NR--,CN--,N.sub.3 --,N.sub.2 -groups or C.dbd.C or C-halogen- or acyl groups with hydrogen on MPc or with a suitable reduction agent on [MPc].sup..crclbar., whereby a platinum metal-phthalocyanine is used as the catalyst. It is possible that by the reversible change (control) of the oxidation phase z of the platinum metal from z.gtoreq.2 to z.ltoreq.1 using the same MPc complex, basically different reductions can be selectively catalysed.Thus the invention concerns a process for selective reduction using platinum metal-phthalocyanine catalysts with reaction specificity in three different reaction patterns.The inventive process is suitable, especially for the synthesis of .alpha.-phenylalkylamines, benzylalkylamines, N-alkyl-amino carboxylic acids, .alpha.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: August 27, 1985
    Inventor: Heiner Eckert
  • Patent number: 4504663
    Abstract: The present invention concerns novel heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: March 12, 1985
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4467089
    Abstract: Novel carbamic and carbonic acid derivatives are provided by simultaneous reaction of a secondary amine and a tertiary amine with carbon dioxide. These derivatives correspond in general to the formula ##STR1## in which R.sub.1 and R.sub.2 may be individual substituents attached to the N or together form with N a heterocyclic moiety; R.sub.3, R.sub.4, R.sub.5 may be individual short chain alkyl or hydroxyalkyl substituents on the N or form therewith a monocyclic or bicyclic heterocyclic moiety. These described compounds find particular use as heat activatable delayed action catalysts especially for use in polyurethane formulations.
    Type: Grant
    Filed: March 4, 1982
    Date of Patent: August 21, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ibrahim S. Bechara
  • Patent number: 4464370
    Abstract: Cyclohexene derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 are hydrogen or tert.-butyl and N and X are members of a heterocyclic ring in which X is an alkylene chain of four, five or six members, one of which may be a hetero-atom, such as oxygen, and where the alkylene radicals are unsubstituted or substituted by alkyl or by --CH.sub.2 OH or its acetyl or propionyl derivative, and their salts are used in fungicides.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: August 7, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Walter Himmele, Christoph Martin, Ernst-Heinrich Pommer, Hardo Siegel
  • Patent number: 4442286
    Abstract: This invention relates to the preparation of amines by the reduction of imines with phosphorous acid, preferably under basic conditions.
    Type: Grant
    Filed: October 15, 1976
    Date of Patent: April 10, 1984
    Assignee: Petrolite Corporation
    Inventor: Derek Redmore
  • Patent number: 4431851
    Abstract: The present invention concerns compounds of the formula ##STR1## wherein n=1, 2 or 3; and R' represents phenyl or orthofluorophenyl. Said compounds are used as intermediates in the preparation of heterocyclic aminoalkyl derivatives which are useful as analgesics and antidepressants.
    Type: Grant
    Filed: March 8, 1983
    Date of Patent: February 14, 1984
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4393209
    Abstract: Decaprenylamines and the acid addition salts thereof, which are useful for controlling virus infection.
    Type: Grant
    Filed: November 19, 1980
    Date of Patent: July 12, 1983
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Hiroyasu Koyama, Yasuhiro Komatsu, Reiko Kubota, Toshihiro Takahashi
  • Patent number: 4386090
    Abstract: The present invention concerns heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.
    Type: Grant
    Filed: December 16, 1981
    Date of Patent: May 31, 1983
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4384116
    Abstract: The invention relates to an improved process for the preparation of fungicidally active compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 individually are lower alkyl of from 1 to 4 carbons or halo-(lower alkyl) of from 1 to 4 carbons or R.sub.1 and R.sub.2 together with the carbon to which they are attached form a 3 to 7 membered cycloalkyl ring or lower alkyl-substituted cycloalkyl of from 4 to 9 carbons, R.sub.3, R.sub.4 and R.sub.5 individually are hydrogen or lower alkyl of from 1 to 4 carbons and X is methylene or oxygen, and salts of those compounds which are basic.The improved process comprises the reaction of a compound of the formula, ##STR2## wherein R.sub.3, R.sub.4, R.sub.5 and X have the significance given hereinabove, with a compound which forms a carbonium ion of the formula ##STR3## wherein R.sub.1 and R.sub.2 have the significance as given hereinabove.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: May 17, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Albert Pfiffner
  • Patent number: 4301284
    Abstract: New N-arylpropyl-substituted amines, and salts, molecular compounds and adducts thereof, having a good fungicidal action, fungicides containing these compounds, and processes for manufacturing these compounds.
    Type: Grant
    Filed: May 18, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Bernd Zeeh, Ernst-Heinrich Pommer, Norbert Goetz
  • Patent number: 4283534
    Abstract: A process for the preparation of aralkylamines of the formula ##STR1## where R.sup.1 is hydrogen, an aliphatic hydrocarbon radical, a cycloaliphatic radical or alkoxy,R.sup.2, R.sup.3 and R.sup.4 are hydrogen or alkyl,X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are hydrogen or alkyl,A is ##STR2## X.sup.5, X.sup.6, X.sup.7, X.sup.8, X.sup.9 and X.sup.10 are hydrogen or alkyl andn is 2, 3 or 4,by reacting a secondary amine with a carbonyl compound in the presence of hydrogen and of a hydrogenation catalyst which comprises palladium, mixed with zinc, cadmium, manganese and/or a rare earth metal oxide, on an inert carrier.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: August 11, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Leopold Hupfer
  • Patent number: 4277471
    Abstract: Biphenylylalkylamines which have anti-arrhythmic activity have been prepared. Pharmaceutical formulations containing such compounds and a method of treating cardiac arrhythmias are provided.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: July 7, 1981
    Assignee: Eli Lilly and Company
    Inventors: William B. Lacefield, Richard L. Simon
  • Patent number: 4260750
    Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.
    Type: Grant
    Filed: March 13, 1980
    Date of Patent: April 7, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Emile Kuntz
  • Patent number: 4241058
    Abstract: Heterocyclic compounds characterized by the formula ##STR1## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X and z are as hereinafter set forth, prepared, inter alia, by reacting a compound characterized by the formula ##STR2## with an amine characterized by the formula ##STR3## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X and Y are as hereinafter set forth, are described. The end products are useful as fungicidal agents.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: December 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Albert Pfiffner
  • Patent number: 4234727
    Abstract: Amines are N-alkylated by reaction with an alcohol or a carbonyl compound in the presence of hydrogen under atmospheric pressure in the gas phase over a catalyst, containing copper and aluminum, which is obtained by heating and reducing a basic precipitate of salts of copper and aluminum.
    Type: Grant
    Filed: August 22, 1979
    Date of Patent: November 18, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Toussaint, Wolfgang Schroeder, Wolfgang Franzischka
  • Patent number: 4226766
    Abstract: A method for preparing N(1)-alkylated-5-phenyl-7-substituted deoxy-1,4-benzodiazepines utilizing a polyphosphoric acid alkyl ester of the formula: ##STR1## wherein R.sub.3 is an alkyl radical with up to 4 carbon atoms as the alkylating agent, is described.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 7, 1980
    Assignee: CRC Compagnia di Recerca Chimica S.A.
    Inventors: Franjo Kajfez, Vitomir Sunjic, Vesna Caplar
  • Patent number: 4220764
    Abstract: Tertiary amines may be prepared by reacting an olefinic compound, carbon monoxide, hydrogen and a heterocyclic compound containing at least one nitrogen atom which possesses at least one hydrogen atom in the presence of a rhodium- or ruthenium-containing catalyst at temperatures in the range of from about 50.degree. to about 350.degree. C. and a pressure in the range of from about 10 to about 300 atmospheres. The reaction may be exemplified by reacting undecene, carbon monoxide, hydrogen and morpholine in the presence of rhodium chloride to prepare N-dodecylmorpholine.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: September 2, 1980
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4204997
    Abstract: A process for the asymmetric synthesis of amines which comprises the amination of a conjugated diene having from 4 to about 20 carbon atoms in the presence of a catalyst system comprising a palladium compound and an optically active phosphine ligand containing at least two phosphorus atoms.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: May 27, 1980
    Assignee: Monsanto Company
    Inventors: Charles F. Hobbs, Dudley E. McMackins
  • Patent number: 4202894
    Abstract: Heterocyclic compounds characterized by the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X and z are as hereinafter set forth,prepared, inter alia, by reacting a compound characterized by the formula ##STR2## with an amine characterized by the formula ##STR3## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X and Y are as hereinafter set forth,are described. The end products are useful as fungicidal agents.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: May 13, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Albert Pfiffner
  • Patent number: 4198510
    Abstract: A process for the preparation of carboxylic acids represented by a formula ##STR1## wherein R.sub.1 represents hydrogen atom or a lower alkyl radical, R.sub.2 represents hydrogen atom, lower alkyl or allyl radical and R.sub.3 represents phenyl, substituted phenyl, substituted naphthyl, dibenzofuranyl or substituted biphenyl. Following novel enamine and amidine compounds as intermediates for manufacturing the carboxylic acids and processes for the manufacture of said enamine and amidine compounds ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the meanings as referred to and R.sub.4 represents dimethylamino, pyrrolidyl, piperidyl or morpholyl.
    Type: Grant
    Filed: July 7, 1978
    Date of Patent: April 15, 1980
    Assignees: Sanwa Kagaku Kenkyusho Co., Ltd., Takayuki Shioiri
    Inventors: Takayuki Shioiri, Nobutaka Kawai, Masatoshi Ban
  • Patent number: 4186148
    Abstract: 3,7-Dimethyl-2,6-octadienylamine derivatives are produced by reacting isoprene with a secondary amine in the presence of a catalyst prepared by reacting a secondary amine, a conjugated diene and/or a polycyclic aromatic compound, a lithium salt and sodium and/or potassium metal.
    Type: Grant
    Filed: May 3, 1978
    Date of Patent: January 29, 1980
    Assignee: Nissan Chemical Industries Limited
    Inventors: Atsuo Murata, Shuji Tsuchiya, Akihiro Konno, Jun Uchida
  • Patent number: 4179469
    Abstract: Amines, which may be utilized in various chemical processes, may be prepared in a combination process wherein the product mixture resulting from the dehydrogenation of a paraffin feed stock may be reacted with a nitrogen-containing compound, carbon monoxide and hydrogen, without separating the olefins in the product mixture, in the presence of certain catalytic compositions of matter to prepare the aforesaid amines.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: December 18, 1979
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4175187
    Abstract: Tertiary allylic amines are obtained from vinylic halides and olefins, and substituted derivatives thereof, by reacting said halide with a mono-, di-, or tri-substituted olefin and an unhindered basic secondary amine in the presence of a palladium catalyst.
    Type: Grant
    Filed: October 24, 1978
    Date of Patent: November 20, 1979
    Assignee: University of Delaware
    Inventor: Richard F. Heck
  • Patent number: 4154852
    Abstract: Novel 7-aminobenzocycloheptenes of the formula ##STR1## wherein X is selected from the group consisting of --NO.sub.2, --NH.sub.2, CH.sub.3 O-- and --OH, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is alkyl of 1 to 5 carbon atoms and R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a saturated heterocycle of 4 to 6 ring carbon atoms optionally containing a second heteroatom in the ring and optionally substituted with an alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts in optically active or racemic mixture form having antidepressant activity and a process for their preparation.
    Type: Grant
    Filed: September 20, 1977
    Date of Patent: May 15, 1979
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Daniel Frechet, Claude Dumont
  • Patent number: 4130590
    Abstract: N-(alkadienyl)amines are produced at a rapid rate and in high yield by the reaction of conjugated dienes with ammonia and amines in a hydroxylic solvent using a catalyst system comprising a palladium compound co-catalyzed with a phosphonite ligand.
    Type: Grant
    Filed: June 21, 1976
    Date of Patent: December 19, 1978
    Assignee: Monsanto Company
    Inventors: Charles F. Hobbs, Dudley E. McMackins
  • Patent number: 4117227
    Abstract: An improved process is disclosed for selectively producing an N-(substituted) morpholine compound from the corresponding N-(substituted) diethanolamine compound. The improved process includes contacting the N-(substituted) diethanolamine compound with a catalytically effective amount of a silica-alumina or certain phosphorus-containing substances at temperatures of from about 190.degree. C to about 260.degree. C under a pressure sufficient to maintain the mixture substantially in liquid phase and recovering from the reaction mixture the formed N-(substituted) morpholine.According to a preferred embodiment, triethanolamine is heated in the presence of a catalytically effective amount of a silica-alumina catalyst having an aluminum content of from about 5 to about 50 wt. % at temperatures of from about 240.degree. C to about 260.degree. C in liquid phase to selectively produce the corresponding N-(hydroxyethyl)morpholine (HEM).
    Type: Grant
    Filed: June 2, 1975
    Date of Patent: September 26, 1978
    Assignee: Texaco Development Corp.
    Inventor: Michael E. Brennan
  • Patent number: 4110447
    Abstract: Compounds of the formulaR--A--Zwherein R is 4-biphenylyl or 4-phenoxyphenyl or a corresponding group monosubstituted or polysubstituted by one or more of F, Cl and Br; A is --CH(CH.sub.3)--CH.sub.2 --(CH.sub.2).sub.n --, --C(CH.sub.3).dbd.CH--(CH.sub.2).sub.n -- or --C(OH) (CH.sub.3)--CH.sub.2 --(CH.sub.2).sub.n --; Z is --NR.sup.1 R.sup.2, imidazol-1-yl, phthalimido or 4,5-dihydro-4-oxophthalazin-1-yl-amino; R.sup.1 and R.sup.2 each are H or alkyl, azaalkyl or acyl, each of 1 - 6 carbon atoms or, collectively, are alkylene of 4 - 7 carbon atoms, 3-oxapentamethylene or 3-R.sup.3 -3-azapentamethylene; R.sup.3 is H or alkyl or hydroxyalkyl each of up to 6 carbon atoms; and n is 0, 1 or 2, and their physiologically acceptable acid addition salts possess anti-inflammatory, anti-arteriosclerotic and serum cholesterol and triglyceride level lowering activities.
    Type: Grant
    Filed: October 22, 1975
    Date of Patent: August 29, 1978
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Joachim Gante, Hans-Adolf Kurmeier, Erich Schacht, Werner Mehrhof, Dieter Orth, Albrecht Wild, Zdenek Simane
  • Patent number: 4105657
    Abstract: Production of N-alkylated cyclic alkylenimines by reaction of cyclic alkylenimines with an alcohol or ether in the gas phase in the presence of a high-area SiO.sub.2 /P.sub.2 O.sub.5 catalyst.
    Type: Grant
    Filed: April 8, 1977
    Date of Patent: August 8, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Herbert Toussaint, Martin Decker
  • Patent number: 4104383
    Abstract: Compounds having psychostimulant, antispasmodic, hypotensive and analgesic properties are disclosed. The compounds have the formula: ##STR1## in which R.sup.2 is selected from the group consisting of a hydrogen atom and a halogen atom;R.sup.1 is selected from the group consisting of a cyclohexyl group and a phenyl group, and is a cyclohexyl group when R.sup.2 is a halogen atom;A is selected from the group consisting of CH.sub.2 CH.sub.2 and CH.dbd.CH groups; andNr.sup.3 r.sup.4 is selected from the group consisting of an alkylamino group, a dialkylamino group and a heterocyclic ring containing from 5 to 7 atoms in the ring, said ring optionally having one or more sbustituents and optionally containing a second hetero-atom; and acid addition salts of said compounds.
    Type: Grant
    Filed: June 4, 1976
    Date of Patent: August 1, 1978
    Assignee: C M Industries
    Inventor: Francois Krausz
  • Patent number: 4104471
    Abstract: A method of producing 1:2 amine-diene adducts which method comprises contacting a sterically unhindered amine with a 1,3 diene in the presence of a catalytic amount of a catalyst comprising an olefin-palladium complex preferably of the type X--Pd--X where X is an olefin and Pd is palladium in its zero valent state.
    Type: Grant
    Filed: March 9, 1977
    Date of Patent: August 1, 1978
    Assignee: Air Products & Chemicals, Inc.
    Inventors: Francis Gordon Albert Stone, Michael Green, Gary Scholes, John Lionel Spencer