Reaction #2122489

Reaction equation

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

sodium cyanide

sodium bicarbonate

water

→

1-methoxy-piperidine-4-carbonitrile

Yield 86.6%

Solvents

dimethylsulfoxide

Conditions

Workup

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

Procedure

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