Water → 1-Methoxypiperidine-4-carbonitrile
Reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6](OS(C)(=O)=O)[CH2:5][CH2:4]1.[C-:14]#[N:15].[Na+].C(=O)(O)[O-].[Na+].O>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([C:14]#[N:15])[CH2:5][CH2:4]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
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.
Workup
- temperatureThen the mixture was cooled to room temperature
- extractionextracted three times with diethyl ether
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent evaporated
- customThe residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1
Sources & evidence
- ORD record
- ord-979cb16aaf744ea7aa02586e523dc5eb
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08574607B2
Reaction notes
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