Sodium borohydride → HCID 15886821, compound

Participants

Reaction Steps

A solution of 4-(oxo)-N-[3-[4-methyl-1-(4-phenyl-1-pipera-zinyl)cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer) (34 mg, 0.072 mmol) in anhydrous EtOH was treated with excess NaBH4 (14 mg, 0.36 mmol) and the resulting solution was stirred at room temperature for 1 h. The reaction was quenched with excess saturated NH4Cl (aq.) then extracted with EtOAc (3×). The combined extracts were dried (Na2SO4), concentrated under reduced pressure, and triturated with 30% EtOAc/hexanes to give 4-(hydroxy)-N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)-cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer), as a white powder. The HCl salt was prepared by adding excess saturated EtOAc/HCl solution to the free base in dry MeOH. Concentration of the homogeneous solution yielded a white solid which was washed with EtOAc. mp=144-145° C.

Provenance & Evidence