Reaction #7689

Reaction equation

4-fluorocinnamic acid

(S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine

EDC

triethylamine

→

title compound

Yield 60.4%

(S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide

Yield 60.4%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1)

Procedure

A solution of 4-fluorocinnamic acid (17 mg, 0.1 mmol), (S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine (24 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), DMAP (12 mg, 0.1 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (2 ml) was stirred at room temperature for 14 h. The reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1) to give the title compound as a solid (26 mg, 60% yield).

Source