Methylamine → N-Methyl-1-(2-methylphenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25° C. was added methylamine (40 % in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25° C. for 30 min after which time it was cooled to 0° C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25° C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired methyl-(2-methyl-benzyl)-amine (10.49 g, 93.2%) as an oil of sufficient purity for use in the next reaction: MS(APCI+) 136.3 m/z (M+H); H-NMR (CDCl3) δ 7.35-7.08 (m, 3 H), 3.73 (s, 2 H), 2.49 (s, 3 H), 2.34 (s, 3 H).

Provenance & Evidence