Benzaldehyde → HCID 69809311, compound

Participants

Reaction Steps

To a solution of 3-(4-chlorophenyl)piperidine in MeOH (0.2 M), benzaldehyde (2.1 eq.) was added and the reaction mixture was stirred at RT for 1 h. Then, it was cooled to 0° C. and NaBH3CN (3 eq.) was added. The mixture was allowed to warm to RT and stirred for 1 h. Evaporation of the solvent gave a residue that was partitioned between sat. aq. NaHCO3 and EtOAc and the organic phase was separated and dried (Na2SO4). Evaporation of the solvent gave a crude that was purified by flash chromatography column on silica (Petroleum ether to EtOAc/Petroleum ether 1:19) yielding (62%) the title compound as a yellow powder. 1H NMR (300 MHz, DMSO-d6, 300K) δ 7.36-7.17 (9H, m), 3.48 (2H, s), 2.87-2.68 (3H, m), 2.05-1.91 (2H, m), 1.86-1.75 (1H, m), 1.74-1.50 (2H, m), 1.48-1.3 (1H, m). MS (ES+) C18H20ClN required: 285, found: 286 (M+H)+.

Provenance & Evidence