Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Isopropyl Acetate | HCID 7915 | — |
| Reactant | (1S)-(+)-Camphor-10-sulphonic acid | HCID 218580 | — |
| Reactant | HCID 58235963 | HCID 58235963 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86663380 | HCID 86663380 | 14% |
Reaction Steps
A mixture of (cis)-benzyl-3-(4-methylpiperazin-1-yl)cyclohexylcarbamate (2.0 g, 6.04 mmol, 1.0 eq.), isopropyl acetate (12 ml) and toluene (2.5 ml) was heated for 15 minutes at 65° C. (1S)-(+) Camphorsulfonic acid (700 mg, 3.02 mmol, 0.5 eq.) and water (0.1 ml) were added at RT and the mixture was heated for 3 hours at 75° C. Stirring was then carried out for 3 hours at RT and the mixture was subsequently allowed to stand overnight at RT for crystallization. The resulting precipitate was filtered off and washed with isopropyl acetate (20 ml). For purification, the desired product was recrystallized from ethanol/isopropyl acetate. Yield: 14% (500 mg, 0.888 mmol)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680159B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-f3fcd0da2aae4c969921caae5885a908 |
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| Source note | uspto-grants-2014_03 |
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