Morpholine → 2-Morpholinomethyl-4-chloropyridine

Participants

Reaction Steps

A mixture of the 2-methyl-4-chloropyridine (1.00 g, 7.84 mmol), NBS (1.42 g, 8.00 mmol) and benzoyl peroxide (˜10 mg) in 10 mL of CCl4 was heated at reflux for 5 h. After cooling down, the reaction mixture was filtered and filtrate was concentrated to give the crude products mixture, which was dissolved in DMF and treated with morpholine (1.00 mL) and K2CO3 (1 g). The mixture was stirred overnight. The mixture was then diluted with EtOAc, washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on SiO2 to give 400 mg of the desired 2-morpholinomethyl-4-chloropyridine.

Provenance & Evidence