2-Morpholinoethanol → 4-(2-Morpholinoethoxy)pyridin-2-amine

Participants

Reaction Steps

2-Morpholinoethanol (2.2 g, 16.8 mmol) was treated with sodium (116 mg, 5.0 mmol) in a sealed tube and stirred at ambient temperature until homogeneous. 4-Chloropyridin-2-amine (1.1 g, 8.9 mmol) was added and reaction heated to 145° C. and stirred in sealed tube for 10 hours. The mixture was cooled to ambient temperature before diluting with ethyl acetate and water. After separation of layers, the aqueous was extracted twice more with ethyl acetate. Concentration of the reaction mixture afforded a viscous oil which was purified on a Biotage 40+ Silica column, eluting with 10% methanol/dichloromethane, to give 4-(2-morpholinoethoxy)pyridin-2-amine as a viscous oil which solidified upon further drying under high vacuum (1.4 g).

Provenance & Evidence