Cesium carbonate → 4-Chloro-2-(3-dimethylaminomethyl-2-ethylphenoxy)benzonitrile fumarate

Participants

Reaction Steps

4-Chloro-2-fluorobenzonitrile (0.82 g, 5.27 mmol), 3-dimethylaminomethyl-2-ethylphenol hydrobromide (1.37 g, 5.27 mmol) and cesium carbonate (3.43 g, 10.5 mmol) were heated with stirring in dry DMF (8 mL) at 50° C. for 4 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with diethyl ether. The ether layer was separated, washed with 1N sodium hydroxide solution (2×), water (3×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to give a yellow oil (1.86 g), which was purified by chromatography to yield 4-chloro-2-(3-dimethylaminomethyl-2-ethylphenoxy)benzonitrile (1.29 g, 78%) as a pale yellow oil. A small portion (98 mg) was converted into the fumarate salt (80 mg, 60%).

Provenance & Evidence