3-(Piperidin-4-yl)pyridine → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-pyridyl)piperidino]butyl]-N-methylbenzamide hydrochloride

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Reaction Steps

Using a procedure similar to that described in Example 1 (alternative procedure), 4-(3-pyridyl)piperidine was alkylated using (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide. Chromatography of the crude product, with dichloromethane:methanol (9:1) as the eluent, followed by conversion to the hydrochloride salt gave the title compound as a white solid (0.253 g); mp 70°-140° C. (dec); NMR: 1.8-2.4 (m, 6), 2.73 (s, 3), 2.8-3.2 (broad s, 5), 7.0-7.2 (m, 3), 7.4 (s, 4), 7.5-7.7 (m, 2), 7.9 (m, 1), 8.2 (broad s, 1), 8.7 (d, 2 J=5); MS: m/z=496(M+1). Analysis for C28H31ClN3O·2.2 HCl·3 H2O: Calculated: C, 53.94; H, 6.31; N, 6.74; Found: C, 53.53; H, 6.16; N, 6.65.

Provenance & Evidence