[BH4-].[Na+].[CH3:3][N:4]([CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13])[CH3:5].Cl>CO>[CH3:5][N:4]([CH:6]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[OH:13])[CH3:3]A total of 28.3 g (747 mmole) sodium borohydride, dissolved in 650 ml methanol, were added in portions to 80.0 g (299 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 (2nd stage), and the mixture was subsequently stirred for one hour. For working up, 680 ml dilute hydrochloric acid (1 N) were added, and the mixture was extracted with 500 ml ether. The aqueous phase was rendered alkaline (pH≧10) with 25 vol. % ammonia solution and extracted three times with 250 ml ether each time. The combined organic extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar). 65.2 g (94% of theoretical) 2-(dimethylaminophenylmethyl)cyclohexanol were obtained.
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