Citric Acid → 1-(4-Dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea citrate

Participants

Reaction Conditions

Reaction Steps

In order to produce the citrate, the more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea (410 mg, 1 mmole) was dissolved in hot ethanol (15 ml) and combined with a likewise hot solution of citric acid (422 mg, 2.2 mmole) in ethanol (2 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. The resultant solid was filtered out. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea citrate was obtained in this manner as a colorless solid (Example 31, melting point: 63-67° C.) in a yield of 588 mg (100%).

Provenance & Evidence