Process for the preparation of heterocyclic alkylamide derivativ

Details Process for the preparation of heterocyclic alkylamide derivativ Process for the preparation of heterocyclic alkylamide derivativ

1995-05-03

1998-03-24

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

546233, 546234, 546567, 546568, C07D21132, C07D26530, C07D20708, C07D20746

Patent

active

057314357

ABSTRACT:
The present invention relates to a novel process for the preparation of N-heterocyclealkanamide derivatives having the following formula: ##STR1## which comprises reacting 1-(2-chloroethyl)piperidine with 2-chlorobenzeneacetonitrile to give (.+-.)-.alpha.-(2-chlorophenyl)-1-piperidinebutanenitrile; alkylating the piperidenebutanenitrile to give (.+-.)-.alpha.-(2-chlorophenyl)-.alpha.-(2,2-dimethoxyethyl)piperidine-1-b utanenitrile; hydrolyzing the resulting alkylated piperidinebutanenitrile to give (.+-.)-.alpha.-(2-chlorophenyl)-.alpha.-(2-oxoethyl)piperidine-1-butanenit rile; reacting the resulting piperidinebutanenitrile with isopropylamine to form eridine-1-butanenitrile; reducing the resulting imine to form peridine-1-butanenitrile; acetylating the resulting amine to form thyl)acetamide; hydrolyzing the resulting acetylated amino substituted piperidine butanenitrile to form yl)-1-piperidinebutanamide; and isolating the resulting piperidinebutanamide.

REFERENCES:
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patent: 5276155 (1994-01-01), Medich et al.
patent: 5432284 (1995-07-01), Dygos et al.
Desai, Bipin, et al. "Synthesis and Structure-Activity Relationships of a New Series of Antiarrhythmic Agents: Monobasic Derivatives of Disobutamide", J. Med. Chem., 31:2158-2164 (1988).

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