Methanol → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-hydroxyphenyl)piperidino]butyl]-N-methylbenzamide hydrochloride

Participants

Reaction Steps

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(3-hydroxyphenyl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide, the title compound was prepared. Chromatography with dichloromethane:methanol followed by conversion to the hydrochloride salt gave a white solid; mp 178°-182° C.; MS: 511; NMR (CD3OD): 1.8-2.3 (m, 6), 2.8 (s, 3), 2.8-3.3 (m, 6), 3.4-3.9 (m, 4), 6.6-6.7 (m, 3), 7.0 (d, J=7, 1), 7.1-7.2 (m, 3), 7.3-7.6 (m, 6); [α]D =-40.3°, c=0.645 (methanol). Analysis for C29H2Cl2N2O2 ·1.0 HCl·0.5 H2O: Calculated: C, 62.54; H, 6.15; N, 5.03; Found: C, 62.19; H, 6.10; N, 5.0.

Provenance & Evidence