反応 #70423

反応方程式

sodium hydrogen carbonate

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

sodium hydrogen carbonate

cyanogen bromide

→

title compound

収率 86.0%

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

収率 86.0%

溶媒

dichloromethane

water

dichloromethane

反応条件

後処理

1. 1
   温度The mixture was cooled in an ice bath
2. 2
   workup.STIRRINGstirred at room temperature for an additional 1 hour
3. 3
   抽出extracted with chloroform
4. 4
   乾燥The organic layer was dried over anhydrous sodium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified by silica gel column chromatography (ethyl acetate)

実験手順

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%).

出典