Starting Materials Include A Nitrogen Containing Hetero Ring (e.g., Starting Materials Include A Piperidine Ring, Etc.) Patents (Class 546/252)
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Patent number: 8946115Abstract: Subject of the invention is a dehydrogenation catalyst for dehydrogenating methylpiperidine to methylpyridine. Subject of the invention are also methods for preparing the catalysts obtained thereby and methods, in which the catalysts are used.Type: GrantFiled: August 29, 2013Date of Patent: February 3, 2015Assignee: Lonza LtdInventors: Daniel Pianzola, Walter Siegrist
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Patent number: 8530664Abstract: Subject of the invention is a dehydrogenation catalyst for dehydrogenating methylpiperidine to methylpyridine. Subject of the invention are also methods for preparing the catalysts obtained thereby and methods, in which the catalysts are used.Type: GrantFiled: October 13, 2010Date of Patent: September 10, 2013Assignee: Lonza Ltd.Inventors: Daniel Pianzola, Walter Siegrist
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Patent number: 8324388Abstract: Processes comprising: providing a dehydrogenatable compound; and subjecting the dehydrogenatable compound to a dehydrogenation reaction at a temperature of from 150 to 400° C., in the presence of oxygen, and at a temperature profile of the dehydrogenation reaction which does not differ substantially from the temperature profile of the dehydrogenation reaction in the absence of oxygen under otherwise identical conditions.Type: GrantFiled: February 7, 2007Date of Patent: December 4, 2012Assignee: BASF AktiengesellschaftInventors: Stefan Kotrel, Martin Ernst
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Patent number: 8247561Abstract: Methyl-2-pentamethylenediamine and methyl-3-piperidine are prepared by hydrogenation of methylglutaronitrile in the presence of a catalyst including cobalt, chromium, and nickel, especially a catalyst based on Raney cobalt doped with nickel and chromium.Type: GrantFiled: March 13, 2009Date of Patent: August 21, 2012Assignee: Rhodia OperationsInventor: Philippe Marion
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Publication number: 20110251397Abstract: The present invention relates to a method for the preparation of 3-methylpyridin by reacting 2-methyl-2,5-di-aminopentane and/or 3-methylpiperidin at about atmospheric pressure and a temperature of 180° C. to 400° C. in a hydrogen atmosphere free of oxygen gas in the presence of a suitable catalyst and of water and/or a volatile alcohol.Type: ApplicationFiled: September 8, 2009Publication date: October 13, 2011Inventors: Anna Maria Cornelia Francisca Castelijns, Pierre Louis Woestenborghs, Henricus Wilhelmus Leonardus Marie Vaessen
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Publication number: 20110034693Abstract: Methyl-2-pentamethylenediamine and methyl-3-piperidine are prepared by hydrogenation of methylglutaronitrile in the presence of a catalyst including cobalt, chromium, and nickel, especially a catalyst based on Raney cobalt doped with nickel and chromium.Type: ApplicationFiled: March 13, 2009Publication date: February 10, 2011Applicant: RHODIA OPERATIONSInventor: Philippe Marion
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Patent number: 7625938Abstract: The present invention relates to substituted pyrazoles, compositions containing such compounds and methods of treatment. The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus.Type: GrantFiled: July 19, 2005Date of Patent: December 1, 2009Assignee: Merck & Co., Inc.Inventors: Linda Brockunier, Jian Guo, Rui Liang, Emma R. Parmee, Subharekha Raghavan, George Scott Tria, Yusheng Xiong
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Patent number: 7439366Abstract: The present invention relates to a phenacylamine derivative of the formula (I) or a salt thereof: wherein A is alkyl, cycloalkyl, phenyl which may be substituted by Y, pyridyl which may be substituted by Y, or pyrazolyl which may be substituted by Y, R1 and R2 are each alkyl, or R1 and R2 may together form a 3- to 6-membered saturated carbocycle, R3 is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl or COR4, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted by Y, phenoxy which may be substituted by Y, benzyloxy which may be substituted by Y, or pyridyloxy which may be substituted by Y, and n is an integer of from 0 to 5.Type: GrantFiled: February 9, 2001Date of Patent: October 21, 2008Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Yuji Nakamura, Masayuki Morita, Kenji Izakura
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Publication number: 20070260065Abstract: A process for preparing phthalimidoamlodipine, which is useful as an intermediate for the preparation of amlodipine and its salts.Type: ApplicationFiled: April 30, 2007Publication date: November 8, 2007Inventors: Vijayabhaskar Bolugoddu, Jaydeepkumar Lilakar Dahyabhai, Ramachandra Reddy Pingili, Madhu Raju Veeraboina, Srinivas Reddy Gade, Srinivas Reddy Mallepalli, Ravindranath Tagore Amirisetty
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Patent number: 6916347Abstract: Primary intermediates for hair coloring compositions for oxidative dyeing of hair are compounds of the formula (1): where R1 and R2 are each individually selected from a hydrogen atom, a C1 to C3 alkyl group, a C1 to C5 mono or dihydroxyalkyl group, phenyl or benzyl optionally substituted with an alkoxy group, or R1 and R2 together with the nitrogen atom to which they are attached form a piperazine, piperidine, imidazole, or morpholine ring.Type: GrantFiled: May 4, 2004Date of Patent: July 12, 2005Assignee: The Procter & Gamble CompanyInventors: Mu-Ill Lim, Yuh-Guo Pan
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Patent number: 6762303Abstract: A method for producing a pyridine compound of formula (II), comprising oxidizing a dihydropyridine compound of formula (I) in the presence of (i) at least one acid and at least one nitrous acid or a nitrite, or (ii) at least one base, and a hydrogen peroxide solution: wherein in formulae (I) and (II), R1 to R5 represents a hydrogen atom, or a substituent; L represents an alkyl group, an alkoxy group, an aryl group, or an aryloxy group.Type: GrantFiled: September 24, 2001Date of Patent: July 13, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Ryo Suzuki, Katsuyoshi Yamakawa
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Patent number: 6667326Abstract: The invention relates to compounds of the general formula wherein R1, R2, R3, R4, R5, X1, X2, X3, m and n have the significances given in claim 1, and optionally the enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for the control of pests on domestic and farm animals.Type: GrantFiled: May 16, 2002Date of Patent: December 23, 2003Assignee: Novartis Animal Health US, Inc.Inventors: Pierre Ducray, Jacques Bouvier, Urs Müller
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Patent number: 6596872Abstract: Described are preferred processes for preparing alkenyl-substituted nitrogenous heterocycles such as vinylpyridines, which comprise reacting a corresponding methyl-substituted heterocycle with a C1 compound such as formadehyde in the vapor phase over a zeolite catalyst having acidic and basic catalytic sites. The preferred zeolite is a medium-pore zeolite, for example having a constraint index of about 0.5 to about 12. Processes of the invention can be conducted as facile, one-step syntheses utilizing relatively low ratios of alkyl-substituted starting heterocycle (e.g. &agr;-picoline or &ggr;-picoline) to formaldehyde while nonetheless achieving high selectivities and yields of the corresponding alkenyl compound.Type: GrantFiled: October 22, 2001Date of Patent: July 22, 2003Assignee: Reilly Industries, Inc.Inventors: Colin H. McAteer, Aaron J. Edwards, Yarlagadda V. Subba Rao
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Patent number: 6566527Abstract: A five-step process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulfonyl)phenyl]ethanone of formula (I): The process involves the following steps: (a) 4-(methylthio)benzyl alcohol is converted into 4-(methylthio)benzyl chloride; (b) 4-(methylthio)benzyl chloride is converted with an alkali metal cyanide into 4-(methylthio)phenylacetonitrile; (c) 4-(methylthio)phenylacetonitrile is condensed with a 6-methyinicotinic ester to give 3-[2-(2-(methylthio)phenyl)-2-cyanoacetyl](6-methyl)pyridine; (d) 3-[2-(4-(methylthio)phenyl-2-cyanoacetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)-phenyl)acetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)phenyl)acetyl(6-methyl)pyridine; and (e) 3-[2(4-(methylthio)phenyl)acetyl](6-methyl)pyridine is oxidized to give the end product.Type: GrantFiled: March 14, 2002Date of Patent: May 20, 2003Assignees: Merck & Co., Inc., Lonza AGInventors: Yves Bessard, James Edward Leresche
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Patent number: 6538139Abstract: Pyrroles of the formula (I) are prepared by dehydrogenating pyrrolidines of the formula (II) where R1 and R2, independently of one another, are hydrogen or an aliphatic radical of 1 to 6 carbon atoms, or pyridines of the formula (III) are prepared by dehydrogenating piperidines of the formula (IV) where R3, R4 and R5, independently of one another, are hydrogen or an aliphatic radical of 1 to 6 carbon atoms, in the presence of a supported noble metal catalyst, by a process in which the dehydrogenation is carried out in the presence of from 1 to 50% by weight, based on the pyrrolidine or piperidine and water, of water.Type: GrantFiled: September 5, 2002Date of Patent: March 25, 2003Assignee: BASF AktiengesellschaftInventors: Martin Schäfer, Arnd Böttcher, Andreas Kramer, Arthur Höhn, Reinhard Kaczmarek, Erhard Henkes
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Patent number: 6509469Abstract: Provided is a process for producing high-purity pyridine derivatives in a high yield at a low cost without causing pollution problems. Pyridine derivatives are produced by reacting 1,2,4-triazine compound with a vinyl carboxylate having a specific structure.Type: GrantFiled: May 29, 2002Date of Patent: January 21, 2003Assignee: Sankio Chemical Co., Ltd.Inventors: Taichi Shintou, Fumiaki Ikeuchi
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Patent number: 6399771Abstract: The invention relates to novel cyclic imines of the formula (I) in which Ar1 and Ar2 each represent substituted phenyl and n represents 1, 2 and 3, to a plurality of processes for their preparation and to their use as pesticides.Type: GrantFiled: September 9, 2000Date of Patent: June 4, 2002Assignee: Bayer AktiengesellschaftInventors: Andrew Plant, Gerd Kleefeld, Thorsten Pötter, Christoph Erdelen, Norbert Mencke, Andreas Turberg, Ulrike Wachendorff-Neumann
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Publication number: 20020065420Abstract: A method for producing a pyridine compound of formula (II), comprising oxidizing a dihydropyridine compound of formula (I) in the presence of (i) at least one acid and at least one nitrous acid or a nitrite, or (ii) at least one base, and a hydrogen peroxide solution: 1Type: ApplicationFiled: September 24, 2001Publication date: May 30, 2002Inventors: Ryo Suzuki, Katsuyoshi Yamakawa
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Patent number: 6365744Abstract: A process for producing a pyridine derivative, which comprises reacting an azametallacyclopentadiene represented by formula (1) with an alkyne in an organic solvent containing a complex of a transition metal such as Ni(II). (In formula (1), M represents an early transition metal, e.g., Zr, Ti or Hf; L represents cyclopentadienyl, indenyl, fluorenyl, hydrocarbon-oxy, amide, acetylacetonato, or carboxy group, a phosphine ligand, an amine ligand, an ether ligand, or a ligand comprising two or more these bonded to each other through appropriate crosslinking group; n is an integer of 1 to 4; and R1, R2, R3, R4 and R5 each represents C1-20 (substituted) alkyl, alkenyl, an aromatic group, silyl, alkoxy, or an ester group.Type: GrantFiled: November 9, 2000Date of Patent: April 2, 2002Assignee: Japan Science & Technology CorporationInventor: Tamotsu Takahashi
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Patent number: 6251827Abstract: Acylsulfamoylbenzamides of the formula I and crop protection compositions comprising them are described. In this formula I, R1, R2, R3, R4 and R5 are various organic radicals and X is CH or N.Type: GrantFiled: September 25, 1998Date of Patent: June 26, 2001Assignee: Hoechst Schering AgrEvo GmbHInventors: Frank Ziemer, Lothar Willms, Thomas Auler, Hermann Bieringer, Christopher Rosinger
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Patent number: 6077956Abstract: The invention relates to a process for preparing 1,2,3,6-tetrahydro-2,2,6,6-tetramethylpyridine from 4-hydroxy-2,2,6,6-tetramethylpiperidine in which 4-hydroxy-2,2,6,6-tetramethylpiperidine is dehydrated at elevated temperature in the gas phase over a solid acid catalyst.Type: GrantFiled: July 24, 1998Date of Patent: June 20, 2000Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Udo Jegelka
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Patent number: 5714610Abstract: In a process for preparing 3-methylpiperidine or 3-methylpyridine from 2-methyl-1,5-diaminopentane in the gaseous phase, the initial product is made to flow over catalysts. In the first step, 3-methylpiperidine is produced, and if required 3-methylpyridine is produced in a second step.Type: GrantFiled: November 2, 1995Date of Patent: February 3, 1998Assignee: Lonza Ltd.Inventors: Josef Heveling, Erich Armbruster, Walter Siegrist
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Patent number: 5554758Abstract: A compound of the formula:A--CH.sub.2 CH.sub.2 --O--B[wherein A stands for an aromatic ring residue, a group shown by R.sup.1 --CO-- (wherein R.sup.1 stands for an aliphatic hydrocarbon residue, aromatic hydrocarbon residue, a heterocyclic residue, an aromatic alipahtic hydrocarbon residue or an alicyclic hydrocarbon residue) or R.sup.2 --CH.dbd.CH-- (wherein R.sup.2 stands for an aliphatic hydrocarbon residue an aromatic hydrocarbon residue a heterocyclic residue an aromatic aliphatic hydrocarbon residue or an alicyclic hydrocarbon residue), and B stands for an aromatic ring residue], can be obtained in high yield, at high purity level by short reaction time, by reacting a compound of the formula:A--CH.sub.2 CH.sub.2 --X(wherein A is of the same meaning as defined above, and X stands for a leaving group) with a compound represented by the general formula:MO--B(wherein M stands for an alkali metal atom or an alkaline earth metal atom and B is of the same meaning as defined above) in a non-aqueous solvent.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Yukio Mizuno, Miichiro Arita
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Patent number: 5463067Abstract: Intermediates of structural formula ##STR1## can be made by reacting glycidol or an activated derivative thereof with an amide. The process and intermediates are useful for synthesizing HIV protease inhibitor compounds.Type: GrantFiled: January 26, 1994Date of Patent: October 31, 1995Assignee: Merck & Co., Inc.Inventors: David Askin, Kan K. Eng, Ralph P. Volante
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Patent number: 5420284Abstract: The title compounds of the formula ##STR1## can be prepared by cyclization of aminomethylenated 2-pentenoic acid derivatives of the formula ##STR2## where R, X, R.sup.1, R.sup.2 and Z have the meaning given in the description,in the presence of acids or ammonia. Preferably, aminomethylenated pentenoic acid derivatives are employed which can be prepared from pentenoic acid derivatives of the formulaR--CH.sub.2 --CH.sub.2 --CH.dbd.CH--Z (III)orR--CH.sub.2 --CH.dbd.CH--CH.sub.2 --Z (IV)with ortho-amides of the formula ##STR3## The meanings of A and B are also given in the description.Type: GrantFiled: October 7, 1993Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hauke Furstenwerth
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Patent number: 5149816Abstract: A process for the selective production of 3-methylpyridine in high yield comprising the step of contacting a vaporized feed stream containing 2-methyl-1,5-pentanediamine with a metal-oxide catalyst of other than an alkali metal at a temperature of about 500.degree.-600.degree. C. for a contact time of less than about 30 seconds. The catalyst may be on a suitable heterogeneous support, and additives in the feed stream may include 3-methylpiperidine as well as water, hydrogen, ammonia, or nitrogen or some other inert gas. A fluid-bed reactor is preferred, with recycling of by-product and continuous effective runs without catalyst regeneration being accomplished at the stated temperatures.Type: GrantFiled: January 4, 1991Date of Patent: September 22, 1992Assignee: Reilly IndustriesInventors: Gerald L. Goe, Robert D. Davis
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Patent number: 4990526Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis, and inhibitors of their biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents, anti-psoriatic agents, and cytoprotective agents.Type: GrantFiled: June 9, 1986Date of Patent: February 5, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Jacques-Yves Gauthier, Richard Frenette
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Patent number: 4935521Abstract: Preparation of 3-picoline from 2-methylglutaronitrile in which the by-products, i.e., 3-methylpiperidine, 2-amino-3-picoline, and 2-amino-5-picoline are recycled and converted to 3-picoline.Type: GrantFiled: April 6, 1989Date of Patent: June 19, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald L. Amey
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Patent number: 4897484Abstract: A process is described for the preparation of compounds of the formula ##STR1## in which R and X are as defined in claim 1. The compounds of the formula (1) are valuable intermediates in the synthesis of triarylmethane dyes and triarylmethanelactones.Type: GrantFiled: December 9, 1987Date of Patent: January 30, 1990Assignee: Ciba-Geigy CorporationInventors: Claus D. Weis, Peter Sutter
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Patent number: 4876348Abstract: Disclosed is a process comprising (1) dehydrocyclization of 2-methylglutaronitrile over Pt or Pd based catalysts to make a mixture containing 3-methylpyridine and lesser amounts of 3-methylpiperidine and (2) reacting such a mixture with NH.sub.3 and O.sub.2 over certain oxide catalysts containing P, V and Mo to obtain 3-cyanopyridine.Type: GrantFiled: October 29, 1985Date of Patent: October 24, 1989Assignee: The Standard Oil CompanyInventors: Robert DiCosimo, James D. Burrington, Dev D. Suresh
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Patent number: 4762929Abstract: Saturated nitrogen-containing five-membered and six-membered heterocycles are aromatized by dehydrogenation in the gas phase in the presence of a supported palladium catalyst containing an alkaline earth metal halide, at from 150.degree. to 350.degree. C. and under from 0.1 to 10 bar.Type: GrantFiled: June 4, 1987Date of Patent: August 9, 1988Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4523016Abstract: The catalytic dehydrogenation of piperidine to pyridine in the gas phase using hydrogen as the carrier gas is carried out with a silicon dioxide carrier activated with copper, nickel and chromium as the catalyst, the metals copper, nickel and chromium being present in an amount of 5-12:1-5:0.1-<0.7 parts by weight per 100 parts by weight of catalyst. The optimum hydrogen/piperidine molar ratio is 5:1, and purified and dried conversion gas from the dehydrogenation reaction is preferably recycled and used as the hydrogen.Type: GrantFiled: July 13, 1983Date of Patent: June 11, 1985Assignee: Rutgerswerke AktiengesellschaftInventors: Georg Grigoleit, Rudolf Oberkobusch, Jurgen Stadelhofer, Kurt Matern
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Patent number: 4401819Abstract: The present invention relates to a process for the preparation of pyridine and substituted pyridines, in the vapor phase. These compounds are obtained by heating, at a temperature of 200.degree. to 500.degree. C., in the vapor phase:piperidine or piperidine substituted by one or more lower alkyl radicals;1,5-diaminopentane;1,5-diaminopentane containing, in its hydrocarbon part, from 1 to 3 linear or branched alkyl radicals having from 1 to 4 carbon atoms; orcompounds such as: N,N'-bis-(piperidin-2-yl)hydrazines,in the presence of a catalyst consisting of palladium, platinum or ruthenium deposited on a macroporous solid.The products obtained by the process according to the invention have various uses. Pyridine is used in particular as a solvent. .beta.-Picoline (or 3-methylpyridine) is used for the preparation of nicotinic acid or nicotinamide, used in pharmacy and in nutrition.Type: GrantFiled: March 22, 1982Date of Patent: August 30, 1983Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Georges Cordier, Patrick Leroux
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Patent number: 4234484Abstract: Special cyclic enamides are prepared by splitting off alcohols catalytically from the corresponding alkoxylated cyclic amides, in the presence of at least one tetraalkylammonium and/or alkali metal salt of tetrafluoroboric acid and/or of hexafluorophosphoric acid as the catalyst, at a temperature of from about 120.degree. to 250.degree. C., distilling off the detached alcohol and isolating the formed enamide in known manner. Particularly preferred starting compounds are those cyclic amides which have been obtained by anodic alkoxylation of corresponding cyclic N-compounds in an alcohol in the presence of supporting electrolytes which are identical with the catalysts subsequently used for splitting off the alcohol, and by distilling off the alcohol from the reaction batch. The enamides are valuable starting products and intermediates for various syntheses, for example, syntheses of prostaglandins and of other pharmaceuticals.Type: GrantFiled: April 25, 1978Date of Patent: November 18, 1980Assignee: Hoechst AktiengesellschaftInventors: Michael Mitzlaff, Klaus Warning
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Patent number: 4196287Abstract: A process for the catalytic production of a 2-substituted pyridine which comprises reacting a corresponding cyano compound and acetylene in the presence of cobaltocene. Favorable conversion speed, conversion of at least 90 percent, good yield and high selectivity are obtained.Type: GrantFiled: October 17, 1977Date of Patent: April 1, 1980Assignee: Lonza Ltd.Inventor: Peter Hardt
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Patent number: 4179570Abstract: A process of preparing alkyl (or aralkyl) pyridines and N-substituted alkyl (or aralkyl) dihydropyridines which comprises treating a2,5,6,8,9-pentaalkyl (or aralkyl) substituted 1,3,7-triazabicyclo (3,3,1) non-3-ene with a Lewis acid.Type: GrantFiled: December 18, 1978Date of Patent: December 18, 1979Assignee: Petrolite CorporationInventor: Bernardus A. Oude Alink
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Patent number: 4169951Abstract: Pyridines substituted in the 2- and 3-positions by aromatic or heteroaromatic groups are prepared by reacting an aromatic or heteroaromatic substituted ketone which has at least one reactive methylene group adjacent to the keto group with an aliphatic oxo compound having a carbon to carbon ethylenic double bond on the carbon atom adjacent to the oxo group and ammonia in the presence of a dehydrating and dehydrogenating catalyst at a temperature of about 250.degree. to 550.degree. C.Type: GrantFiled: September 6, 1977Date of Patent: October 2, 1979Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Helmut Beschke, Heinz Friedrich