Acetic Acid → N-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-2-(3,5-difluoro-phenyl)-acetamide

Participants

Reaction Steps

To a stirred solution of 4-{[2-(3,5-difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine (0.038 g, ˜0.08 mmol) in ClCH2CH2Cl (0.5 mL) at room temperature under Ar was added cyclopropanecarboxaldehyde (0.008 mL, 0.096 mmol, 1.2 eq.) and HOAc (0.05 mL, 1% v/v). The mixture was stirred for 0.5 h then Na(OAc)3BH (0.026 g, 0.12 mmol, 1.5 eq.) was added and the mixture stirred for 16 h then diluted with EtOAc (5 mL) and washed with saturated aqueous NaHCO3 solution (5 mL) and saturated brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, and dried under high vacuum to give N-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-2-(3,5-difluoro-phenyl)-acetamide (0.040 g, 0.76 mmol, 95%). MS (ESI): 525.2/526.2 (M+1).

Provenance & Evidence