Sodium Sulfate → 1-benzyl-N'-indan-5-yl-N,N-dimethylcyclohexane-1,4-diamine

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Reaction Steps

266 mg 5-aminoindane and 462 mg 4-benzyl-4-dimethylamino-cyclohexanone (see example 3) were dissolved in dry 1,2-dichloroethane under argon and the solution was stirred with 2 g sodium sulfate for 24 hours at RT. 600 mg sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for two hours at RT. For working up, the reaction mixture was concentrated and the residue was adjusted to pH 11 with five molar sodium hydroxide solution. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (4×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product was chromatographed over silica gel with ethyl acetate. 440 mg 1-benzyl-N′-indan-5-yl-N,N-dimethyl-cyclohexane-1,4-diamine were obtained as a colorless oil. For preparation of the hydrochloride, the base was dissolved in 2-butanone (8 ml), and 1.85 M ethanolic hydrochloric acid (1.75 ml) was added. The solid which had precipitated out was filtered off with suction and dried. 280 mg 1-benzyl-N′-indan-5-yl-N,N-dimethyl-cyclohexane-1,4-diamine hydrochloride were obtained as a white solid (m.p. 200-203° C.)

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