Cesium carbonate → (2-Fluoro-4-nitrophenyl)-(3-imidazol-1-ylpropyl)amine

Participants

Reaction Steps

To a solution of 1-(3-chloropropyl)-1H-imidazole (1.90 g, 13.14 mmol), cesium carbonate (4.28 g, 13.14 mmol) and a catalytic amount of KI in DMF (30 mL) cooled in an ice-bath was added 2-fluoro-4-nitroaniline (1.38 g, 8.84 mmol) in one portion. At the end of addition, the mixture was refluxed and stirred further for 36 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo. To the residue was added water (50 mL) and the resulting mixture was extracted with DCM (20 mL×2). The combined organic layers were washed with brine (20 mL×2) and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=15:1) to give the title compound as yellow oil (2.85 g, 82%).

Provenance & Evidence