Reaction #2329080

Reaction equation

4-hydroxy-1-methylpiperidine

sodium hydride

3,4-Difluoronitrobenzene

→

title compound

Yield 38.0%

4-(2-fluoro-4-nitrophenoxy)-1-methylpiperidine

Yield 38.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 3 hours
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   WashThe ethyl acetate layer was washed with saturated brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherThe solvent was evaporated under reduced pressure

Procedure

A solution of 4-hydroxy-1-methylpiperidine (0.30 g, 2.65 mmol) in anhydrous tetrahydrofuran (6 ml) was added dropwise to a suspension of 60% sodium hydride (0.054 g, 2.27 mmol) in anhydrous tetrahydrofuran (6 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. 3,4-Difluoronitrobenzene (0.30 g, 1.89 mmol) was added to the reaction mixture under ice cooling, and the mixture was refluxed for 3 hours. Ice water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.18 g, 38%) as a yellow crystal.

Source