Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Benzoic acid, 4-fluoro-, ethyl ester | HCID 67976 | — |
| Reactant | HCID 178461287 | HCID 178461287 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 178468979 | HCID 178468979 | 70.2% |
Reaction Steps
A mixture of cis-1-(4-methylcyclohexyl)piperazine (29.6 g), ethyl 4-fluorobenzoate (41.0 g) and potassium carbonate (67.3 g) in DMSO (300 ml) was stirred at 140° C. for 9 hours. The reaction mixture was poured into water (1.2 l) and extracted twice with ethyl acetate (400 ml). The extracts were collected, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (2:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give ethyl 4-[cis-4-(4-methylcyclohexyl)-1-piperazinyl]benzoate (37.64 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06884774B2 |
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| Source dataset | uspto-grants-2005_04 |
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| ORD ID | ord-bdb2bf9adbdb48148604455ae2d381d0 |
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| Source note | uspto-grants-2005_04 |
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