HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 66731655, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | Dimethyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-1,4-dicarboxylate | HCID 66734961 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66731655 | HCID 66731655 | 99% |
Reaction Steps
Dimethyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-1,4-dicarboxylate (5.35 g, 14.10 mmol) was dissolved in acetonitrile (100 mL) and water (2.000 mL), then lithium bromide (9.80 g, 112.84 mmol) was added. Triethylamine (7.82 mL, 56.42 mmol) was added and the resulting suspension was heated under reflux for 7 h. MTBE (350 mL) and water (180 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 3.8 M HCl and extracted with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated. 2-(2-Fluoro-4-(trifluoromethoxy)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (5.09 g, 99%) was yielded as a colorless solid. MS m/z 364 (M−H)−
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415378B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-c2551da773344ad2b2b50f9b831e0e24 |
| Source note | uspto-grants-2013_04 |