Cyclohexanone → 1-Cyclohexylpyrrolidine

HRID 1264445

反応式

HRID 1264445 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.S([O-])([O-])(=O)=O.[Mg+2]>CCCCCC>[CH:6]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 7967CyclohexanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31268Pyrrolidine

生成物 1

HCID 1390641-Cyclohexylpyrrolidine

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

The structure-directing agent (SDA) is synthesized using the reaction sequence described in the scheme below. A three neck 3000-ml flask is charged with 100 gm (1.4 mole) of pyrrolidine, 50 gm of cyclohexanone (0.51 mole) and 1000 ml anhydrous hexane. To the resulting solution, 122 gm (1.022 mole) of anhydrous magnesium sulfate is added and the mixture is mechanically stirred and heated at reflux (the reaction is monitored by NMR analysis) for 96 hrs. The reaction mixture is filtered through a fritted glass funnel. The filtrate is concentrated under reduced pressure on a rotary evaporator to give 75 gm of a clear (yellow-tinted) oily substance. 1H-NMR and 13C-NMR spectra are acceptable for the desired product 1-(1-pyrrolidino)cyclohexene. Saturation of 1-(1-pyrrolidino)cyclohexene, to give N-cyclohexylpyrrolidine, is accomplished in quantitative yield by hydrogenation in ethanol at a 55 psi pressure of hydrogen gas in the presence of 10% Pd on activated carbon.

後処理

  1. customThe structure-directing agent (SDA) is synthesized
  2. temperatureheated
  3. temperatureat reflux (the reaction
  4. customfor 96 hrs
  5. filtrationThe reaction mixture is filtered through a fritted glass funnel
  6. concentrationThe filtrate is concentrated under reduced pressure on a rotary evaporator
  7. customto give 75 gm of a clear (yellow-tinted) oily substance

出典と根拠

ORDレコード
ord-c35b202f270447d795b3589653b53f82
出典データセット
uspto-grants-2003_04
特許番号
US06544495B1

関連ノート

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