Reaction #70423

Reaction equation

sodium hydrogen carbonate

4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine

sodium hydrogen carbonate

cyanogen bromide

→

title compound

Yield 86.0%

4-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-carbonitrile

Yield 86.0%

Solvents

dichloromethane

water

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled in an ice bath
2. 2
   workup.STIRRINGstirred at room temperature for an additional 1 hour
3. 3
   Extractionextracted with chloroform
4. 4
   DryingThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was purified by silica gel column chromatography (ethyl acetate)

Procedure

To a solution of 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine (124 mg, 0.358 mmol) in dichloromethane (1 mL) was added a solution of sodium hydrogen carbonate (60 mg, 0.716 mmol) in water (0.5 mL). The mixture was cooled in an ice bath followed by the addition of a solution of cyanogen bromide (45 mg, 0.430 mmol) in dichloromethane (1 mL). The mixture was stirred at 0° C. for 30 minutes and then stirred at room temperature for an additional 1 hour. The mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (114 mg, yield 86%).

Source