Acetic Acid → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-ethoxycarbonyl-4-(2-oxopiperidino) piperidino]butyl]-N-methylbenzamide hydrochloride

Participants

Reaction Steps

(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (415 mg) in methanol (3 mL) was added to a solution of 4-ethoxy-carbonyl-4-(2-oxopiperidino) piperidine (391 mg) and acetic acid (0.09 mL) in methanol (6 mL). After 15 minutes, sodium cyanoborohydride (100 mg) in methanol (3 mL) was added in a single portion. After being stirred for 3 hours, the reaction mixture was diluted with aqueous sodium bicarbonate, stirred for 30 minutes, and extracted with dichloromethane. The organic extracts were dried, evaporated, and chromatographed, with dichloromethane:methanol (95:5) as eluent. The resulting material was dissolved in dichloromethane, precipitated out as the hydrochloride salt with ethereal hydrogen chloride, evaporated, and placed under high vacuum overnight to give the title compound as a white solid (630 mg); MS: m/z=588(M+l). Analysis for C31H39Cl2N3O4 ·1.70 HCl·0.20 (C2H5)2O: Calculated: C, 57.40; H, 6.46; N, 6.31; Found: C, 57.40; H, 6.37; N, 6.17.

Provenance & Evidence