HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-Methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-{4-[(Cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride | HCID 66911519 | — |
| Reactant | 2-Methyl-5-(trifluoromethyl)phenyl chlorocarbonate | HCID 86660232 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate | HCID 86660231 | — |
Reaction Steps
At room temperature, 2-methyl-5-(trifluoromethyl)phenyl chlorocarbonate (239 mg) is added to a solution of 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride (VII-1, 324 mg) and diisopropylethylamine (323 mg) in dichloromethane (8 ml). The mixture is stirred at room temperature overnight, and water is then added. The aqueous phase is separated off and extracted with ethyl acetate, and the combined organic phases are then dried with sodium sulphate. The solid is filtered off and the solvent is removed by distillation. The residue is purified chromatographically. This gives 2-methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (193 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08501781B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-69fc3fec76814f3190d3425460196ab9 |
| Source note | uspto-grants-2013_08 |