HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 66731707, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | HCID 86646599 | HCID 86646599 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66731707 | HCID 66731707 | 89% |
Reaction Steps
Dimethyl 2-(2-chloro-4-fluorophenyl)piperidine-1,4-dicarboxylate (2.5 g, 7.58 mmol) was dissolved in acetonitrile (50 mL) and water (1 mL), then lithium bromide (5.27 g, 60.65 mmol) was added. Triethylamine (4.20 mL, 30.33 mmol) was added and the resulting suspension was heated under reflux for 7 h. MTBE (170 mL) and water (90 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-Chloro-4-fluorophenyl)-1-(methoxycarbonyl)-piperidine-4-carboxylic acid (2.130 g, 89%) was isolated as a brown solid. MS m/z 316 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415378B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-4f540b3577164809bf48cf0362480990 |
| Source note | uspto-grants-2013_04 |