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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence