Diethyl Ether → 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea

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Reaction Steps

The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea (219 mg, 0.5 mmole) was dissolved in ethyl methyl ketone (40 ml). Chlorotrimethylsilane (95 μl, 0.75 mmole) was added dropwise with stirring at RT. After one hour's stirring at RT, no precipitate had formed. The reaction solution was reduced to 5 ml under a vacuum and combined with diethyl ether (15 ml). The mixture was then vigorously stirred at RT for 1 h. An almost colorless precipitate was formed. The solid was filtered out, washed with diethyl ether (3×3 ml) and dried under a vacuum. The hydrochloride of the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-urea (219 mg, m.p. 170-174° C., 93%; Example 26) was obtained in this manner as a colorless solid.

Provenance & Evidence