2-(Dimethylamino)ethanol → 4-[2-(Dimethylamino)ethoxy]-3-(trifluoromethyl)benzenamine

In 6 mL of dimethylformamide, 256 mg (2.87 mmol) of 2-dimethylaminoethanol was dissolved, and 42 mg (1.05 mmol) of sodium hydride was added thereto, and the mixture solution was stirred at room temperature for 10 minutes, and then 200 mg (0.96 mmol) of 2-fluoro-5-nitrobenzotrifluoride was added thereto and the mixture solution was heated at 50° C. for two hours. The reaction solution was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride solution. To the organic layer, 20 mg of 10% palladium carbon and 2 mL of methanol were added, and the mixture solution was stirred at room temperature in a hydrogen atmosphere at normal pressures for 16 hours. After filtration, the filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain 230 mg (97%) of a yellow oily target product.

1. temperaturethe mixture solution was heated at 50° C. for two hours
2. extractionextracted with ethyl acetate
3. washthe extract was washed with a saturated sodium chloride solution
4. additionTo the organic layer, 20 mg of 10% palladium carbon and 2 mL of methanol were added
5. stirringthe mixture solution was stirred at room temperature in a hydrogen atmosphere at normal pressures for 16 hours
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated
8. customthe residue was purified by silica gel column chromatography

ORD record

ord-39faa4672ed245e49d47a78e7c6583d9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609656B2