Sodium Carbonate → 1-(2-(5-Pyrimidinyl)-prop-2-yl)-4-oxopiperidine

HRID 2294944ノート

反応式

HRID 2294944 の反応式
[N:1]1[CH:6]=[C:5]([C:7]([NH2:10])([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[I-].C[N+]1(C)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)C>[N:1]1[CH:6]=[C:5]([C:7]([N:10]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 111494971,1-Dimethyl-4-oxopiperidin-1-ium iodideHCID 450801402-(Pyrimidin-5-yl)propan-2-amine

生成物 1

HCID 214715951-(2-(5-Pyrimidinyl)-prop-2-yl)-4-oxopiperidine収率 34.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a stirred mixture of 2-(5-pyrimidinyl)-2-propylamine (660 mg), ethanol (9 mL) and K2CO3 (665 mg) heated to reflux was added dropwise over 30 min, a solution of 1,1-dimethyl-4-oxopiperidinium iodide (1.9 g) in water (36 mL). When the addition was complete, the mixture was heated under reflux for an additional 2 h, cooled, basified to pH 10 with Na2CO3 and extracted with ethyl acetate (3 .Yen.100 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Column chromatography over silica gel, eluting with a methylene chloride; 5% methanol gave 360 mg of 1-(2-(5-pyrimidinyl)-prop-2-yl)-4-oxopiperidine as an oil: 1H NMR (400 MHz, CDCl3) 9.13 (s, 1H), 8.95 (s, 2H), 2.79 (t, 4H), 2.44 (t, 4H), 1.47 (s, 6H).

後処理

  1. temperatureheated
  2. temperatureto reflux
  3. additionwas added dropwise over 30 min
  4. additionWhen the addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for an additional 2 h
  7. temperaturecooled
  8. extractionextracted with ethyl acetate (3 .Yen.100 mL)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. washColumn chromatography over silica gel, eluting with a methylene chloride

出典と根拠

ORDレコード
ord-2be575fc1c034a92b43d4da955ac96e3
出典データセット
uspto-grants-1997_11
特許番号
US05691323

反応ノート

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