Water → HCID 14551559, compound

Participants

Reaction Steps

To a stirred solution of [4-(1H-imidazol-1-yl)phenyl][1-[2-(3,4-dimethoxyphenyl)ethyl]-4-piperidinyl]methanone (5.90 g, 14.1 mmol) in methanol (100 ml) at 0° C. was added sodium borohydride (1.80 g, 47.6 g mmol) in three equal portions over a 24 hour period. Water was added and the solution was concentrated to a white suspension. This aqueous suspension was extracted twice with dichloromethane. The combined organic layers were dried (MgSO4), and filtered through a pad of silica gel (eluting with acetone). The eluent was concentrated and the resulting solid was recrystallized from tetrahydrofuran to afford α-[4-(1H-imidazol-1-yl)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-piperidine methanol (2.9 g, 49%): m.p. 59°-60° C.

Provenance & Evidence