Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[CH:13]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)=O.[BH4-].[Na+]>[OH-].[Na+].C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:12][CH2:13][C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)([CH3:10])[CH3:11])=[CH:7][CH:8]=1A mixture of 1-(4-chlorophenyl)-1-methylethylamine hydrochloride (2.7 g) was dissolved in 2M sodium hydroxide solution (50 ml) and the amine free base was extracted into diethyl ether to give an oil. This oil was dissolved in absolute ethanol (15 ml) and 2-formylimidazole (1.5 g) in absolute ethanol (20 ml) was added dropwise. The mixture was boiled under reflux for 4 hours and then left to stand at ambient temperature for 48 hours. Sodium borohydride (0.67 g) was added in portions to the solution and the mixture was boiled under reflux with stirring for 7 hours. The ethanol was removed under reduced pressure and water (40 ml) added to the residue. The mixture was filtered to give 1-(4-chlorophenyl)-N-(imidazol-2-ylmethyl)-1-methylethylamine, m.p. 164-165° C.
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