Methylamine → N,2-Dimethyl-4-pyridinemethanamine

Participants

Reaction Steps

A stirred solution of 0.86 g (6.98 mmol) of 2-methyl-4-hydroxymethylpyridine (R. B. Katz et al., Synthetic Communications, 19, 1989, 317-325) in 48% aqueous HBr was heated at reflux for four days. The reaction mixture was cooled and added dropwise to 20 ml of 40% aqueous methylamine. The volatiles were removed under reduced pressure, and the residue was slurried in CH2Cl2 and then filtered. The filter cake was washed with CH2Cl2, EtOAc, CH3CN, and 10% MeOH in CH3CN. The filtrate was concentrated, and the residue was flash chromatographed on silica, eluting CH2Cl2 :NH3 -saturated MeOH (9:1). Consequently, 0.65 g (68% yield) of methyl-(2-methyl-pyridin-4-ylmethyl)-amine (39) was obtained as a colorless liquid.

Provenance & Evidence