Ethanol → N-Methyl[1,1′-biphenyl]-3-methanamine

Participants

Reaction Conditions

Reaction Steps

Into a 250-mL round-bottom flask was placed methanol (100 mL), acetic acid (42 mL), Biphenylcarboxaldehyde (7.96 g, 43.7 mmol, 1 equiv), methylamine in anhydrous ethanol (20 g, 193.2 mmol, 4.4 equiv), and NaBH3CN (8.3 g, 132.1 mmol, 3 equiv). The solution was stirred overnight at 60° C. The resulting solution was diluted with 200 mL of water and extracted with 3×200 mL of ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10) to give N-methyl (3-biphenyl)methylamine as a colorless oil.

Provenance & Evidence