Water → 1-Methoxypiperidine-4-carbonitrile

HRID 2035307ノート

反応式

HRID 2035307 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 667939701-Methoxypiperidine-4-carbonitrile収率 86.6%

試薬・触媒・溶媒 2

HCID 165872Tetrabutylammonium Cyanide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-979cb16aaf744ea7aa02586e523dc5eb
出典データセット
uspto-grants-2013_11
特許番号
US08574607B2

反応ノート

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