3-(pyridin-4-yl)benzaldehyde → N-methyl(3-(pyridin-4-yl)phenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

Into a 250 mL round-bottom flask was placed a solution of 3-(pyridin-4-yl)benzaldehyde (10 g, 54.6 mmol, 1 equiv) in MeOH (200 mL), NaBH3CN (10.33 g, 164 mmol, 3 equiv) and CH3NH2.HCl (18.44 g, 273 mmol, 5 equiv). The mixture was stirred overnight at 60° C. The solvents were removed under reduced pressure. The residue was added to 100 mL of H2O and extracted with 5×200 mL of ethyl acetate. After removal of solvent, the crude product was purified by re-crystallization from ethyl acetate to give 5 g of N-methyl-(3-(pyridin-4-yl)phenyl)methylamine as a white solid.

Provenance & Evidence