Tryptamine → HCID 86601797, compound

Participants

Reaction Steps

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, [4-(2-aminoethyl)-1-phenylcyclohexyl]dimethylamine (491 mg, 2 mmole) 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 the expected diastereoisomers and could be purified by column chromatography [silica gel 60 (100 g); MeOH (1000 ml)]. The more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea was obtained as a colorless oil in a yield of 330 mg (36%). The more nonpolar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea was obtained as a colorless oil in a yield of 230 mg (25%).

Provenance & Evidence