1-Benzyl-4-piperidone → 1-Benzyl-4-propylidenepiperidine

HRID 1737431노트

반응식

HRID 1737431 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:3]=[CH2:4].C([Li])CCC.[CH2:29]([N:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH2:29]([N:36]1[CH2:41][CH2:40][C:39](=[CH:2][CH2:3][CH3:4])[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 192201-Benzyl-4-piperidoneHCID 197740Allyltriphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 149666551-Benzyl-4-propylidenepiperidine수율 17.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a stream of argon, 2.9 g (7.5 mmol) of allyltriphenylphosphonium bromide was suspended in 10 ml of anhydrous tetrahydrofurane, and thereto 4.3 ml of butyllithium a was added dropwise under cooling with ice. After stirring the mixture at room temperature for 30 minutes, thereto was added dropwise a solution of 1 g (5.3 mmol) of 1-benzyl-4-piperidone in anhydrous tetrahydrofurane under cooling with ice and the obtained mixture was stirred at room temperature for 15 hours. The reaction solution was filtrated, and ethyl acetate 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 40 g of silica gel and eluted with ethyl acetate-hexane (1:1 to 1:3) to obtain 200 mg of 1-benzyl-4-propylidenepiperidine.

후처리

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

출처 및 근거

ORD 기록
ord-7845f52371564048adaa27537172da7e
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962476

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