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US 4,118,393 AGranted
Phenyl azabicyclohexanones
AssigneeAmerican Cyanamid Company
InventorsWilliam Joseph Fanshawe, Sidney Robert Safir, Lantz Stephen Crawley
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Abstract
Substituted phenyl azabicyclohexanones, their method of preparation, and their conversion into substituted phenyl azabicyclohexanes which are active anxiolytic and analgesic agents.
Claims12
An optically active compound of the formulae:
- ##STR5## wherein the phenyl moiety is unsubstituted, mono- or di-substituted from the group consisting of halogen, straight chain C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, nitro, amino, trifluoromethyl, acetamido and hydroxy;
- and the racemic mixture thereof.
A method for the preparation of an optically active compound of the formulae:
- ##STR6## wherein the phenyl moiety is unsubstituted, mono- or di-substituted from the group consisting of halogen, straight chain C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, nitro, amino, trifluoromethyl, acetamido and and the racemic mixture thereof;
- which comprises reducing a phenyl cyano ester of the formulae:
- ##STR7## wherein the phenyl moiety is unsubstituted, mono- or di-substituted as previously defined and R is selected from the group consisting of C.sub.1 -C.sub.6 alkyl;
- with diborane, in a solvent, at a temperature from about 0.degree. to about 60.degree. C., from about one to about three hours;
- and reacting the intermediate reduction product with a mineral acid.
2 more elements
Dependencies are inferred from the claim text.