Reacción #70423

Ecuación de reacción

sodium hydrogen carbonate

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

sodium hydrogen carbonate

cyanogen bromide

→

title compound

Rendimiento 86.0%

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

Rendimiento 86.0%

Disolventes

dichloromethane

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente