Acetic Acid → HCID 10298721, compound

Participants

Reaction Steps

5-Benzyloxytryptamine (440 mg, 1.65 mmol) were dissolved in 1,2-dichloroethane (14 ml) under argon (slightly cloudy solution). After addition of 4-dimethylamino-4-phenylcyclohexanone (359 mg, 1.65 mmol) and glacial acetic acid (189 μl, 3.3 mmol), the mixture was stirred for two hours at RT. Sodium triacetoxyborohydride (462 mg) was then added and the suspension was stirred for four days at RT. For working up, water (15 ml) was added to the reaction mixture. The phases were separated and the aqueous phase was washed with ether (20 ml) and then rendered strongly alkaline with sodium hydroxide solution. The aqueous phase was extracted with ether (2×10 ml) and ethyl acetate (4×10 ml), the combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (686 mg) was recrystallized from a mixture of ethyl acetate/cyclohexane (35 ml/5 ml). 396 mg N′-[2-(5-benzyloxy-1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture (m.p. 130-134° C.).

Provenance & Evidence