HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzylaminomethyl]-4-methoxyphenyl]propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(Bromomethyl)-4-(trifluoromethyl)benzene | HCID 123062 | — |
| Reactant | Ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochloride | HCID 22139981 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzylaminomethyl]-4-methoxyphenyl]propanoate | HCID 11122720 | 32.4% |
Reaction Steps
To a solution of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-ethylpropanoate hydrochloride (203 mg, 0.673 mmol) in N,N-dimethylformamide (4 mL), potassium carbonate (232 mg, 1.68 mmol) and 4-(trifluoromethyl)benzyl bromide (169 mg, 0.707 mmol) were added, and then the mixture was stirred for 3 hours at room temperature and for 4 hours under heating at 60° C. After cooling, the mixture was poured in ice water, which was extracted with diethyl ether. The organic later was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1 v/v) to afford 92.3 mg (32%) of the title compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07049342B2 |
| Source dataset | uspto-grants-2006_05 |
| ORD ID | ord-4e2d6a6033d44936b638deac44b9860e |
| Source note | uspto-grants-2006_05 |