1,2-Dichloroethane → HCID 9925137, compound

Participants

Reaction Steps

1.12 g tryptamine and 1.52 g 4-dimethylamino-4-phenylcyclohexanone were dissolved in dry tetrahydrofuran (12 ml) and 1,2-dichloroethane (40 ml) under argon. Glacial acetic acid (801 μl) and 1.92 g sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for four days at RT. For working up, the reaction mixture was concentrated and the residue was taken up in water (20 ml), two molar hydrochloric acid (5 ml) and ether (35 ml). The aqueous phase was separated off, washed with ether (2×15 ml), adjusted to pH 11 with sodium hydroxide solution and extracted with ethyl acetate (3×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The beige-brown residue obtained (2.0 g) was chromatographed over silica gel with methanol which contained 0.75 vol. % triethylamine. 553 mg of the nonpolar diastereomer of N′-[2-(1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained (m.p. 175-178° C.), from which the corresponding dihydrochloride was obtained with chlorotrimethylsilane in 2-butanone/acetone (20 ml/50 ml) (600 mg; m.p. 216-218° C.).

Provenance & Evidence