1-(2-Chloroethyl)piperidine → 2-(2-Chlorophenyl)-4-(piperidin-1-yl)butanenitrile
Reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]#[N:19]>>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:18]#[N:19]Participants
3
Procedure
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 (±)-α-(2-chlorophenyl)-1-piperidinebutanenitrile; alkylating the piperidenebutanenitrile to give (±)-α-(2-chlorophenyl)-α-(2,2-dimethoxyethyl)piperidine-1-butanenitrile; hydrolyzing the resulting alkylated piperidinebutanenitrile to give (±)-α-(2-chlorophenyl)-α-(2-oxoethyl)piperidine-1-butanenitrile; reacting the resulting piperidinebutanenitrile with isopropylamine to form (±)-α-(2-chlorophenyl)-α-[2-[(1-methylethyl)imino]ethyl]piperidine-1-butanenitrile; reducing the resulting imine to form (±)-α-(2-chlorophenyl)-α-[2-[(1-methylethyl)amino]ethyl]-piperidine-1-butanenitrile; acetylating the resulting amine to form (±)-N-[3-(2-chlorophenyl)-3-cyano-5-(1-piperidinyl)pentyl]-N-(1-methylethyl)acetamide; hydrolyzing the resulting acetylated amino substituted piperidine butanenitrile to form (±)-α-[2-[acetyl(1-methylethyl)amino]ethyl]-α-(2-chlorophenyl)-1-piperidinebutanamide; and isolating the resulting piperidinebutanamide.