Water → trans-1-Benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine

Participants

Reaction Steps

To the hydrochloride salt of rac-trans-3-(m-chlorophenyl)-4-phenylpiperidine (CAS Reg. No.: [134823-41-9]) (500 mg) in methylene chloride (10 mL) triethylamine (677 μL) and benzenesulfonyl chloride (229 μL) were added. The reaction mixture was stirred at room temperature for 4 h, water was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 3:1) yielded trans-1-benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine (0.66 g, 98%) as a white foam, MS: 411 (M, 1 Cl).

Provenance & Evidence