Acetic Acid → N1,N1-dimethyl-5-(trifluoromethyl)benzene-1,3-diamine

In 3 mL of methanol, 150 mg (0.55 mmol) of N-(3-amino-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide, 0.076 mL (0.9 mmol) of a 37% formaldehyde aqueous solution and 0.05 mL of acetic acid were dissolved, and 47 mg (0.74 mmol) of sodium cyanoborohydride was added thereto, and the mixture solution was stirred at room temperature for 15 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride solution and concentrated, and the residue was dissolved in 6 mL of tetrahydrofuran. To this solution, 10 mL of a saturated sodium bicarbonate solution was added and the mixture solution was heated at 50° C. for 20 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the extract was dried on anhydrous magnesium sulfate and concentrated, and the residue was purified by silica gel column chromatography to obtain 100 mg (89%) of a brownish oily target product.

1. extractionextracted with ethyl acetate
2. washthe extract was washed with a saturated sodium chloride solution
3. concentrationconcentrated
4. dissolutionthe residue was dissolved in 6 mL of tetrahydrofuran
5. additionTo this solution, 10 mL of a saturated sodium bicarbonate solution was added
6. temperaturethe mixture solution was heated at 50° C. for 20 hours
7. additionThe reaction solution was poured into water
8. extractionextracted with ethyl acetate
9. dry with materialthe extract was dried on anhydrous magnesium sulfate
10. concentrationconcentrated
11. customthe residue was purified by silica gel column chromatography

ORD record

ord-8bf656079b0a4de2901e53f97fc74625

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609656B2