[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:15]N.C(O)C.[BH3-][C:21]#[N:22].[Na+]>O.C(O)(=O)C.CO>[CH3:15][NH:22][CH2:21][C:13]1[CH:14]=[C:9]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:10]=[CH:11][CH:12]=1Into 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.
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