Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Citrate | HCID 31348 | — |
| Reactant | HCID 86601797 | HCID 86601797 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86601799 | HCID 86601799 | — |
Reaction Steps
In order to produce the citrate, the more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea (330 mg, 0.71 mmole) was dissolved in hot ethanol (4 ml) and combined with a likewise hot solution of citric acid (137 mg, 0.71 mmole) in ethanol (1 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. Since no solid precipitated out, the ethanol was removed by distillation. The more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)-ethyl]thiourea citrate was obtained in this manner as a colorless foam (Example 44, melting point: 90-95° C.) in a yield of 467 mg (100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07348354B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-8a17d929c2704fe59c2cc9a50f1d9c7c |
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| Source note | uspto-grants-2008_03 |
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