Réaction #2122489

Équation de réaction

Methanesulfonic acid 1-methoxy-piperidin-4-yl ester

sodium cyanide

sodium bicarbonate

water

→

1-methoxy-piperidine-4-carbonitrile

Rendement 86.6%

Solvants

dimethylsulfoxide

Conditions de réaction

Traitement

1. 1
   TempératureThen the mixture was cooled to room temperature
2. 2
   Extractionextracted three times with diethyl ether
3. 3
   SéchageThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Autrethe solvent evaporated
5. 5
   AutreThe residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1

Mode opératoire

200 mg Methanesulfonic acid 1-methoxy-piperidin-4-yl ester (from Step 2), 251 mg tetrabutylammonium cyanide and 272 mg sodium cyanide were mixed in 1 ml dimethylsulfoxide, and heated to 55° C. for 18 hours. Then the mixture was cooled to room temperature, 1 ml saturated aqueous sodium bicarbonate and 3 ml water were added, and extracted three times with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1, then 2:1, then pure ethyl acetate) as a solvent. 116 mg 1-methoxy-piperidine-4-carbonitrile was obtained.

Source