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

Participants

Reaction Steps

A solution of 6-bromopyridine-2-carbaldehyde (3 g, 16.13 mmol) and morpholine (1.405 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 in vacuo. The resulting material was purified by silica gel chromatography (30-100% ethyl acetate/hexanes) which afforded the title compound. LRMS (APCI) calc'd for C10H13BrN2O [M+1]+: 257, Found: 257.

Provenance & Evidence