[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1.[BH4-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([OH:10])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1To a stirred solution of 25 g (0.076 mol) of the 1-methyl-3-phenyl-4-(4-chlorophenacyl) piperazine in 450 ml of ethanol was added in portions 2.9 (0.076 mol) of sodium borohydride. The resulting mixture was stirred at ambient temperature for 2 hours, poured into 50% aqueous sodium chloride and extracted with ethyl acetate. The organic extracts were combined, washed with water and saturated sodium chloride and dried over sodium sulfate. The resulting crude product obtained from concentration of the filtrate was subjected to rapid liquid chromatography on a silica gel column to give 16 g (60% overall) of 1-methyl-3-phenyl-4-[2-hydroxy-2-(4-chlorophenyl)ethyl]piperazine as a white solid.
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