Acetic Acid → HCID 67751248, compound

Participants

Reaction Conditions

Reaction Steps

A solution of cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpiperidine (220 mg, 0.75 mmol, Example 2) and acetic acid (0.212 ml) in dry methanol (6 ml) was cooled to 0° C. and sodium cyanoborohydride (96 mg, 1.5 mmol) was added followed by formaldehyde (38% aq. solution, 0.15 ml). The reaction mixture was stirred at 23° C. for 18 h, then the solvent was removed in-vacuo and the residue partitioned between dichloromethane and 2M sodium hydroxide. The layers were separated, and the aqueous phase extracted with dichloromethane (2×20 ml). The combined organic extracts were washed with water then brine, then dried (K2CO3) and concentrated to leave a clear oil. Purification on silica-gel (CH2Cl2 /MeOH/NH3 97:3:0.5 then CH2Cl2 /MeOH 90:10) provided the title compound as a clear, colourless oil. 1H NMR (CDCl3) 7.42 (m), 7.30 (m), 6.77 (s), 6.54 (s), 4.27 (d, J=12.2 Hz), 4.04 (d, J=12.2 Hz), 3.42 (s), 3.07 (m), 2.91 (d, J=1.9 Hz), 2.17 (s), 2.10 (m) 2.04 (s), 1.56 (m), 1.39 (m). MS (CI) m/z 310 (MH).

Provenance & Evidence