Water → 1-Methoxypiperidine-4-carbonitrile

HRID 2035307노트

반응식

HRID 2035307 반응식
[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]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 86663299Methanesulfonic acid 1-methoxy-piperidin-4-yl ester

생성물 1

HCID 667939701-Methoxypiperidine-4-carbonitrile수율 86.6%

시약·촉매·용매 2

HCID 165872Tetrabutylammonium Cyanide촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
55 °C

실험 절차

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.

후처리

  1. temperatureThen the mixture was cooled to room temperature
  2. extractionextracted three times with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent evaporated
  5. customThe residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1

출처 및 근거

ORD 기록
ord-979cb16aaf744ea7aa02586e523dc5eb
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08574607B2

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