Reaction #2329084

Reaction equation

Water

Propionyl chloride

triethylamine

1-(2-fluoro-4-nitrophenyl)piperazine

→

title compound

Yield 53.0%

1-[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]propan-1-one

Yield 53.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe organic layer was washed with saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe residue obtained by evaporation of the solvent under reduced pressure
5. 5
   Otherwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Procedure

Propionyl chloride (0.620 g, 4.88 mmol), triethylamine (0.747 ml, 5.32 mmol) and 4-dimethylaminopyridine (0.0542 g, 0.444 mmol) were added to a solution of 1-(2-fluoro-4-nitrophenyl)piperazine (compound of Reference Example 52; 1.00 g, 4.44 mmol) in anhydrous tetrahydrofuran (9 ml) under ice cooling, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (0.662 g, 53%) as a yellow solid.

Source