Acetic Acid → 1-(4-bromo-3-fluorophenyl)-N-methyl-2-(4-morpholinyl)ethanamine

Temperature

40 °C

To an ambient temperature solution containing 1.52 g of 1-(4-bromo-3-fluorophenyl)-2-(4-morpholinyl)ethanone (5.04 mmols) in 25 mL of THF was added 10.1 mL of MeNH2 (20.2 mmols, 2M solution in THF). After stirring for 15 min. 0.66 mL of acetic acid and 1.27 g of NaCNBH3 (20.2 mmols) were added to the reaction mixture. The reaction mixture was then warmed to 40° C. and stirred for 24 h. The reaction mixture was quenched with 10% aqueous Na2CO3 (10 mL). The reaction was diluted with 100 mL of EtOAc, and the layers were separated. The organic layer was washed with 10% aqueous Na2CO3 (1×10 mL) and saturated aqueous brine solution (1×10 mL). The organics were then dried over MgSO4, filtered through a frit, and concentrated. The crude title product was isolated as a brown solid (1.6 g, ˜100%) and used without further purification. MS (ES) m/e 317 [M+H]+.

1. stirringstirred for 24 h
2. customThe reaction mixture was quenched with 10% aqueous Na2CO3 (10 mL)
3. additionThe reaction was diluted with 100 mL of EtOAc
4. customthe layers were separated
5. washThe organic layer was washed with 10% aqueous Na2CO3 (1×10 mL) and saturated aqueous brine solution (1×10 mL)
6. dry with materialThe organics were then dried over MgSO4
7. filtrationfiltered through a frit
8. concentrationconcentrated

ORD record

ord-fe1e1bcedba2426ea32a9918c8729a8e

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749998B2