Patents Assigned to CONTRAF-NICOTEX-TOBACCO GMBH
  • Preparation of racemic nicotine by reaction of ethyl nicotinate with N-vinylpyrrolidone in the presence of an alcoholate base and subsequent process steps
    Patent number: 11407730
    Abstract: The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.
    Type: Grant
    Filed: December 18, 2018
    Date of Patent: August 9, 2022
    Assignees: Siegfried AG, Contraf-Nicotex-Tobacco GmbH
    Inventors: Beat Theodor Weber, Christian Lothschütz, Ben Pan
  • Enantiomeric separation of racemic nicotine by addition of an O,O?-disubstituted tartaric acid enantiomer
    Patent number: 11279685
    Abstract: The present invention relates to a method of separating racemic nicotine of Formula (1-a) as a mixture of the (R)- and (S)-enantiomers into the enantiomerically pure (S)- and (R)-nicotine represented by Formula (1-b) and (1-c), by adding a mixture of the L- and the D-enantiomer of a O,O?-disubstituted tartaric acid, wherein the molar ratio of the L- to the D-enantiomer is from 80:20 to 95:5, and obtaining the (S)-nicotine of formula (1-b), or by adding O,O?-dibenzoyl-D-tartaric acid and obtaining the (R)-nicotine of formula (1-c).
    Type: Grant
    Filed: December 18, 2018
    Date of Patent: March 22, 2022
    Assignees: SIEGFRIED AG, CONTRAF-NICOTEX-TOBACCO GMBH
    Inventors: Beat Theodor Weber, Ben Pan
  • Preparation of racemic nicotine by reaction of ethyl nicotinate with N-vinylpyrrolidone in the presence of an alcoholate base and subsequent process steps
    Patent number: 11091458
    Abstract: The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.
    Type: Grant
    Filed: December 18, 2018
    Date of Patent: August 17, 2021
    Assignees: Siegfried AG, Contraf-Nicotex-Tobacco GmbH
    Inventors: Beat Theodor Weber, Christian Lothschütz, Ben Pan
  • PREPARATION OF RACEMIC NICOTINE BY REACTION OF ETHYL NICOTINATE WITH N-VINYLPYRROLIDONE IN THE PRESENCE OF AN ALCOHOLATE BASE AND SUBSEQUENT PROCESS STEPS
    Publication number: 20200331884
    Abstract: The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.
    Type: Application
    Filed: December 18, 2018
    Publication date: October 22, 2020
    Applicants: SIEGFRIED AG, CONTRAF-NICOTEX-TOBACCO GMBH
    Inventors: Beat Theodor Weber, Christian Lothschütz, Ben Pan
  • ENANTIOMERIC SEPARATION OF RACEMIC NICOTINE BY ADDITION OF AN O,O'-DISUBSTITUTED TARTARIC ACID ENANTIOMER
    Publication number: 20200331883
    Abstract: The present invention relates to a method of separating racemic nicotine of Formula (1-a) as a mixture of the (R)- and (S)-enantiomers into the enantiomerically pure (S)- and (R)-nicotine represented by Formula (1-b) and (1-c), by adding a mixture of the L- and the D-enantiomer of a O,O?-disubstituted tartaric acid, wherein the molar ratio of the L- to the D-enantiomer is from 80:20 to 95:5, and obtaining the (S)-nicotine of formula (1-b), or by adding O,O?-dibenzoyl-D-tartaric acid and obtaining the (R)-nicotine of formula (1-c).
    Type: Application
    Filed: December 18, 2018
    Publication date: October 22, 2020
    Applicants: SIEGFRIED AG, CONTRAF-NICOTEX-TOBACCO GMBH
    Inventors: Beat Theodor WEBER, Ben PAN