Triethylamine → 1-(4-Dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea

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Reaction Steps

Phenylpropylamine (285 μl, 2 mmole) was dissolved in dry chloroform (15 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, the diastereoisomer mixture of N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine was added and stirring was 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-(3-phenyl-propyl)-thiourea was obtained as a colorless foam in a yield of 205 mg (25%). The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea was obtained as a colorless foam in a yield of 410 mg (50%).

Provenance & Evidence