Allyl bromide → N,N-Diethylbenzamide

HRID 538269

반응식

HRID 538269 반응식
[CH:1]([N:14]1[CH2:19][CH2:18]N[CH2:16][CH2:15]1)(C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)C=C.C(=O)([O-])[O-:25].[Na+].[Na+]>O1CCCC1>[CH2:15]([N:14]([CH2:19][CH3:18])[C:1](=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:16]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 70048Benzhydrylpiperazine

생성물 1

HCID 15542N,N-Diethylbenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The mixture of benzhydrylpiperazine epimers (7.6 g, 14.9 mmol) was dissolved in 50 mL of dry tetrahydrofuran with 1.6 mL (18.6 mmol) of allyl bromide and 5.1 g (36.9 mmol) of sodium carbonate and stirred at room temperature under nitrogen for 2 days. The reaction solution was poured into ice water/ethyl acetate and separated. The organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved in a small amount of dichloromethane and placed on a column of silica gel. The diastereomers were separated by elution with a stepwise gradient of ethanol in dichloromethane. The first isomer was eluted with 1.3% ethanol in dichloromethane, and the second isomer was obtained with 1.6% ethanol in dichloromethane. Fractions containing the second isomer were combined and the solvent removed in vacuo to give 1.44 g of 4-(αR)-α-((2R,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-N,N-diethylbenzamide as a brown oil.

후처리

  1. customseparated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in a small amount of dichloromethane
  5. customThe diastereomers were separated by elution with a stepwise gradient of ethanol in dichloromethane
  6. washThe first isomer was eluted with 1.3% ethanol in dichloromethane
  7. customthe second isomer was obtained with 1.6% ethanol in dichloromethane
  8. additionFractions containing the second isomer
  9. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-405eaa2d14644a6b99fa266ea55b0770
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865721B2

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