Acetic Acid → HCID 9925137, compound

Participants

Reaction Steps

Tryptamine (320 mg) was dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 4-dimethylamino-4-phenylcyclohexanone (435 mg), glacial acetic acid (229 μl) and sodium triacetoxyborohydride (550 mg), the suspension was stirred for 3 days at RT. For working up, water (20 ml) was added to the reaction mixture. The organic phase was separated off and the aqueous phase was extracted once with ether and then rendered strongly alkaline with sodium hydroxide solution. The aqueous phase was milky-cloudy at pH 10. It was extracted with ethyl acetate (4×10 ml), the extracts were combined, dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (674 mg) was recrystallized twice from ethyl acetate (5 ml). 22 mg of the nonpolar diastereoisomer of N′-[2-(1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained (m.p. 134-138° C.).

Provenance & Evidence