[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])[C:13](=[O:15])[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O.Cl>C(O)C.CC(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:16]([CH3:17])[CH3:18])[CH:13]([OH:15])[CH3:14])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one (1.9 g prepared as described in Example 47) in ethanol (10 ml) was added dropwise to a suspension of sodium borohydride (0.4 g) in ethanol (20 ml) and the mixture was stirred for 4 hours at ambient temperature. 5N Sulphuric acid (10 ml) was added and then the acidified mixture was basified. The resulting mixture was extracted with ether and the ether extracts were washed with water and dried. Removal of the solvent gave an oil which was converted into a hydrochloride salt by treatment with a mixture of excess concentrated hydrochloric acid and propan-2-ol. The residue after the removal of the solvents was dried by azeotropic distillation with propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-ol hydrochloride (m.p. 255° C.).
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