HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetone → tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Pentafluorophenol | HCID 13041 | — |
| Reactant | (Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid | HCID 66598895 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylate | HCID 86647187 | 95% |
Reaction Steps
(Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid (108 mg, 0.267 mmol) was dissolved in ethyl acetate:acetone=4:1 (5.7 mL). At room temperature, pentafluorophenol (59 mg, 0.320 mmol) and N,N′-dicyclohexylcarbodiimide (66 mg, 0.320 mmol) were added sequentially, and the mixture was stirred at room temperature for 10 hours. The reaction solution was added water, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (129 mg (yield 95%)) was obtained as a white crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08551985B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-697fe3c805b24cee81438b07c3744455 |
| Source note | uspto-grants-2013_10 |