Morpholine → 2-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-2-ethylsulfanyl-6-methyl-benzonitrile (0.9 g, 4.26 mmol) in dioxane (90 ml) are added morpholine (0.56 g, 6.39 mmol) and sodium tert-butoxide (1.2 g, 12.8 mmol). The reaction mixture is degassed and flushed with Argon for 30 min and then (2-biphenyl)di-tert-butylphosphine (0.25 g, 0.85 mmol) and bis(dibenzylideneacetone)-palladium(0) (0.5 g, 0.85 mmol) are added. The reaction mixture is stirred at 100° C. for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture is filtered through a pad of celite pad. The filtrate is concentrated to get the crude product, which is purified by column chromatography (silica gel, 5% acetone/hexane) to yield 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzonitrile (0.30 g, 1.14 mmol, 27%).

Provenance & Evidence