反应详情

温度

-5 °C

α-methyltryptamine (261.4 mg, 1.5 mmole) was dissolved in dry chloroform (15 ml) and combined with triethylamine (422 μl, 3 mmole). The mixture was cooled to −5° C. Thiophosgene (115 μl, 1.5 mmole) dissolved in chloroform (10 ml) was then added dropwise, resulting in the formation of a precipitate. After a reaction time of 18 h at RT, (4-aminomethyl-1-phenyl-cyclohexyl)-dimethylamine (348.55 mg, 1.5 mmole) dissolved in chloroform (10 ml) was added. After 20 h stirring at RT, the reaction mixture was clear. Working up was performed by washing the batch with saturated NaHCO3 solution (3×5 ml) and water (5 ml). The organic phase was dried with Na2SO4 and evaporated. The product was a mixture of two diastereoisomers. These were purified and separated by column chromatography [silica gel 60 (70 g); eluent: MeOH/EE 1:5 (1500 ml)]. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]thiourea (177 mg, m.p. 99-104° C., 26%) and also the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methylethyl]thiourea (152 mg, m.p. 93-95° C., 23%) were colorless solids.

1. additionwas then added dropwise
2. customresulting in the formation of a precipitate
3. additionwas added
4. washby washing the batch with saturated NaHCO3 solution (3×5 ml) and water (5 ml)
5. dry with materialThe organic phase was dried with Na2SO4
6. customevaporated
7. additiona mixture of two diastereoisomers
8. customThese were purified
9. customseparated by column chromatography [silica gel 60 (70 g); eluent: MeOH/EE 1:5 (1500 ml)]