Morpholine → 4-Morpholinobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 4-fluorobenzonitrile (1.00 g, 8.26 mmol) and morpholine (0.77 mL, 9.08 mmol) in dimethyl sulfoxide (40 mL) was treated with 37% KF on alumina, and the mixture was heated at 150° C. for 5 h. After cooling, the mixture was diluted with EtOAc and filtered through diatomaceous earth. The filtrate was washed with water (3×), brine (1×), and then dried with magnesium sulfate. The extract was concentrated and the residue was purified by chromatography (SiO2, 20 to 30% EtOAc in hexanes) yielding 930 mg (60%) of the title compound.

Provenance & Evidence