Water → N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine

Participants

Reaction Steps

Cyclohexylamine (0.30 mL) and sodium bicarbonate (259 mg) were sequentially added to a solution of 6-[(4-tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine (200 mg) in acetonitrile (4 mL) at room temperature, and then the mixture was heated under reflux for six hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:50→1:10) to give N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine as a pale yellow amorphous (201 mg, 87%).

Provenance & Evidence