Acetic Acid → [1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

Participants

Reaction Steps

1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone (4.45 g, 16.6 mmol) and methyl amine (33 mL, 66.4 mmol of 2 M solution in THF) were dissolved in 75 mL THF and maintained for 15 minutes at room temperature. NaBH3CN (3.13 g, 49.8 mmol) was added and the reaction mixture was treated with 1 mL acetic acid and stirred at room temperature for 4 days. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.7 g (99%) of the title compound as a yellow oil. MS (ES) m/e 284 [M+H]+.

Provenance & Evidence