Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Citrate | HCID 31348 | — |
| Reactant | HCID 86601794 | HCID 86601794 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86601795 | HCID 86601795 | — |
Reaction Steps
In order to produce the citrate, the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea (256 mg, 0.59 mmole) was dissolved in hot ethanol (8 ml) and combined with a likewise hot solution of citric acid (249 mg, 1.3 mmole) in ethanol (1 ml). After cooling to approx. 5° C., the batch was left to stand for 4 h. The resulting solid was filtered out. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea citrate could be obtained in this manner as a colorless solid (Example 34, melting point: 108-113° C.) in a yield of 369 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-d21f6caa31c2497ab2a51629d1dc02d9 |
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| Source note | uspto-grants-2008_03 |
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