Acetic Acid → HCID 10155518, compound

Participants

Reaction Steps

292 mg C-(1H-Indol-3-yl)-methylamine were partly dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 463 mg 4-benzyl-4-dimethylamino-cyclohexanone (see example 3), glacial acetic acid (4 mmol) and sodium triacetoxyborohydride (550 mg), the suspension was stirred for 72 hours at room temperature. For working up, water (10 ml) was added to the reaction mixture. The organic phase was separated off and the aqueous phase was extracted twice with ether and then rendered strongly alkaline with sodium hydroxide solution. It was extracted again with ethyl acetate (4×10 ml). A pale precipitate precipitated out of the combined ethyl acetate phases even during the processing. After cooling, this was filtered off with suction, washed twice with cold ethyl acetate and dried. 235 mg 1-benzyl-N′-(1H-indol-3-ylmethyl)-N,N-dimethyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture (m.p. 194-198° C.).

Provenance & Evidence