METHOD OF MAKING A BENZYLPROPANAMINE

A method of making (R)-N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorobenzene)prop anamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy- alpha -me...

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Hauptverfasser: NELSON, WILLIAM, A, DUFF, STEVEN, R, D'AMBRA, THOMAS, E, VANWAGENEN, BRADFORD, C
Format: Patent
Sprache:eng ; fre
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Zusammenfassung:A method of making (R)-N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorobenzene)prop anamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy- alpha -methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have formula (1) wherein R, R1, R2 and R3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl. A method of making (R)-N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy- alpha -methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have formula (1) wherein R, R1, R2 and R3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl. L'invention concerne un procédé de production de (R)-N-[1-(3-méthoxyphényl)éthyl]-3-(2-chlorobenzène)propanamine qui fait appel à la réduction du précurseur amidyle ou iminyle approprié avec un agent de réduction approprié. Le précurseur amidyle ou iminyle approprié est obtenu par synthèse, au moyen de (R)-3-méthoxy- alpha -méthylbenzylamine. Un procédé de condensation d'un nitrile avec une amide primaire ou secondaire, pour former une imine, consiste à faire réagir un nitrile avec de l'hydrure de diisobutylaluminium, puis à faire réagir le composé ainsi obtenu avec une amine primaire ou secondaire pour former l'imine désirée. On fait particulièrement appel à ce procédé pour produire des imines énantiomériquement pures, et, finalement, des amines. Des amines de ce type répondent à l