[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.[OH-].[Na+]>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[OH:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=14-Benzamido-(4-phenyl-4-oxobutyl)piperidine (3.4 g.) was dissolved in methanol (125 ml.) and a solution of sodium borohydride (6.0 g.) in 0.2 N sodium hydroxide (30 ml.) was added at room temperature over a period of 0.5 hours. The resulting mixture was stirred for a further 2 hours and then heated under reflux for 4 hours. The resulting mixture was filtered, the filtrate evaporated almost to dryness and then treated with water (100 ml.). The colourless solid was filtered off, washed with water, dried, dissolved in a small amount of ethanolic hydrogen chloride and treated with ether until crystallisation commenced. Filtration and drying gave 1.875 g. of the hydrochloride of the title compound, m.p. 221° C. (Found: C, 68.1; H, 7.4; N, 7.3. C22H28N2O2.HCl requires C, 67.9; H, 7.5; N, 7.2%).
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