Methylamine → N-Methylpyridine-4-methylamine

Participants

Reaction Steps

To 4-picolyl chloride, hydrochloride (10 g, 0.06 mol) was added methylamine (50 mL of 40% aqueous solution, 0.58 mol), and the resulting purple solution was stirred at rt for 30 min, then poured into H2O. The mixture was extracted with CH2Cl2 (6×), and the combined organic extracts were evaporated. The residue was filtered under reduced pressure through a silica gel column, eluting with a solvent gradient of 0-10% MeOH/CHCl3 to provide the title compound as a light yellow oil (4.8 g, 66%): 1H NMR (CDCl3): d 8.50 (dd, 2H); 7.20 (dd, 2H); 3.70 (s, 2H); 2.40 (s, 3H); 1.70 (br, 1H).

Provenance & Evidence