Tryptamine → HCID 86601791, compound

Participants

Reaction Steps

2-(1H-Indol-3-yl)-ethylamine (tryptamine; 320 mg, 2 mmole) was dissolved in dry chloroform (10 ml) and combined with triethylamine (555 μl, 4 mmole). Thiophosgene (153 μl, 2 mmole) was added to this mixture. After a reaction time of 16 h, N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine was added and stirring continued for a further 16 h at RT. Working up was performed by extracting the batch with saturated NaHCO3 solution (3×20 ml). The organic phase was dried with Na2SO4 and evaporated. The product was a mixture of two diastereoisomers and could be purified by column chromatography [silica gel 60 (50 g); methanol (500 ml)]. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-ethyl]-thiourea was obtained as a colorless foam in a yield of 185 mg (22%). The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-ethyl]-thiourea was obtained as a colorless foam in a yield of 433 mg (52%).

Provenance & Evidence