Potassium Carbonate → HCID 43267162, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-(chloromethyl)pyridine (318 mg, 1.96 mmole) in 4 mL of dry acetonitrile is 395 mg (3.92 mmol) of N-methylcyclopentylamine followed by 270 mg (1.96 mmol) of potassium carbonate. The reaction is heated at 80° C. for 20 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 340 mg (77% yield) of (6-Chloro-pyridin-3-ylmethyl)-cyclopentyl-methyl-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.40–1.90 (m, 4H), 2.15 (s, 3H), 2.78–2.89 (m, 1H), 3.56 (s, 2H), 7.29 (d, 1H, J=8.3 Hz), 7.70–7.80 (m, 1H), 8.28 (d, 1H, J=2.1 Hz); MS 225.3 (M+H).

Provenance & Evidence