Reaction #2329087

Reaction equation

sodium hydrogencarbonate

formaldehyde

formic acid

3-(2-fluoro-4-nitrophenoxymethyl)piperidine

→

title compound

Yield 87.0%

3-(2-fluoro-4-nitrophenoxymethyl)-1-methylpiperidine

Yield 87.0%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   DryingThe organic layer was dried over anhydrous sodium sulfate
3. 3
   OtherThe residue obtained by evaporation of the solvent under reduced pressure
4. 4
   Otherwas purified by column chromatography on silica gel

Procedure

38% aqueous formaldehyde (1.00 ml) and formic acid (1.00 ml) were added to 3-(2-fluoro-4-nitrophenoxymethyl)piperidine (compound of Reference Example 53; 0.300 g, 1.18 mmol), and the mixture was stirred at 90° C. for 1 hour. The reaction mixture was adjusted to pH=8 by addition of saturated aqueous sodium hydrogencarbonate, diluted with water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel to give the title compound (0.275 g, 87%) as a yellow solid.

Source