Acetyl chloride → HCID 67751568, compound

Participants

Reaction Steps

Acetyl chloride (0.26 ml, 3.66 mmol) was added dropwise with stirring to anhydrous methanol (3.7 ml) and the resultant solution was added to a solution of cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpiperidine (360 mg, 1.22 mmol) in anhydrous methanol (1 ml). The solvent was removed in vacuo, and the residue recrystallised from ethyl acetate-methanol to provide cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenyl piperidine hydrochloride salt as a crystalline, white solid, m.p.=200°-225° C. (decomp). 1H NMR (360 MHz, DMSO-d6) δ7.44 (m), 6.82 (2), 6.56 (2), 4.49 (2), 4.41 (d, J=12.3 Hz), 4.09 (d, J=12.3 Hz), 3.80 (s), 3.05 (t, J=14.7 Hz), 2.14 (s), 1.90 (m), 1.72 (m); m/z (CI+) 296 (MH); Analysis: Found: C, 72.36; H, 7.91; N, 4.31. Calcd. for C20H26NOCl; C, 72.38; H, 7.90; N, 4.22%.

Provenance & Evidence