Morpholine → 4-((6-Bromopyridin-2-yl)methyl)morpholine

Participants

Reaction Steps

Reductive Amination Method A: A solution of 6-bromopyridine-2-carbaldehyde (3 g, 16.13 mmol) and morpholine (1.41 mL, 16.13 mmol) in 1,2-dichloroethane (22 mL) under argon was charged with sodium triacetoxyborohydride (4.79 g, 22.58 mmol) and allowed to stir for 14 hours. The reaction mixture was then diluted with ethyl acetate (100 mL), saturated aqueous sodium bicarbonate (60 mL), and saturated aqueous sodium carbonate (90 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (2×50 mL), dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by silica gel chromatography (30-100% ethyl acetate/hexanes) to afford the title compound as a white solid.

Provenance & Evidence