Potassium Carbonate → N-methyl-tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-(chloromethyl)pyridine (570 mg, 3.52 mmole) in 7 mL of dry acetonitrile is 608 mg (7.04 mmol) of N-methyl-t-butylamine followed by 486 mg (3.52 mmol) of potassium carbonate. The reaction is heated at 80° C. for 12 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 420 mg (56% yield) of N-methyl-tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.14 (s, 9H), 2.06 (s, 3H), 3.48 (s, 2H), 7.26 (d, 1H, J=6.2 Hz), 7.68 (d, 1 h, J=6.6 Hz), 8.28 (d, 1H, J=2.5 Hz); MS 213.3 (M+H).

Provenance & Evidence