1-Benzyl-4-piperidone → 1-Benzyl-4-benzylidenepiperidine

HRID 53664

反応式

HRID 53664 の反応式
Cl.[CH:2](=[C:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[CH2:20](N1CCC(=O)CC1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:20]([N:12]1[CH2:13][CH2:14][C:9](=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

6

反応物 3

HCID 192201-Benzyl-4-piperidoneHCID 185390104-Benzylidenepiperidine hydrochlorideHCID 178418339Butyllithium

生成物 1

HCID 218433641-Benzyl-4-benzylidenepiperidine

試薬・触媒・溶媒 2

HCID 70671Benzyltriphenylphosphonium chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Synthesis of 4-benzylidenepiperidine hydrochloride (1) In a stream of argon, 49.0 g (126 mmol) of benzyltriphenylphosphonium chloride was suspended in 100 ml of anhydrous tetrahydrofurane, and thereto 86 ml of butyllithium was added dropwise under cooling with ice. After stirring the mixture at room temperature for 1 hour, thereto was added dropwise a solution of 1-benzyl-4-piperidone in anhydrous tetrahydrofurane under cooling with ice and the obtained mixture was refluxed with heating for 15 hours. The reaction solution was filtrated, and diethyl ether and water were added to the filtrate, and the organic phase was taken out. The organic phase was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting oily matter was subjected to a column chromatography using 1 kg of silica gel and eluted with ethyl acetate-hexane (1:100 to 3:100) to obtain 22.6 g of 1-benzyl-4-benzylidenepiperidine.

後処理

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. temperaturethe obtained mixture was refluxed
  4. temperaturewith heating for 15 hours
  5. filtrationThe reaction solution was filtrated
  6. additiondiethyl ether and water were added to the filtrate
  7. washThe organic phase was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. washeluted with ethyl acetate-hexane (1:100 to 3:100)

出典と根拠

ORDレコード
ord-76a3d0f5602843f29b9987c0655944f4
出典データセット
uspto-grants-1997_04
特許番号
US05620994

関連ノート

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