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Water → 1-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid

HRID 1620602
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HRID 1620602 반응식
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][CH2:4][NH:3]1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[C:25]([F:28])([F:27])[F:26].O>O1CCCC1>[F:26][C:25]([F:27])([F:28])[C:16]1[CH:17]=[C:18]([C:21]([F:24])([F:22])[F:23])[CH:19]=[CH:20][C:15]=1[CH2:14][N:3]1[CH2:4][CH2:5][CH:6]([C:8]([OH:10])=[O:9])[CH2:7][C:2]1=[O:1]
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 552860802-Oxopiperidine-4-carboxylic acid

생성물 1

HCID 866787731-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carboxylic acid수율 58.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To a solution of 2-oxopiperidine-4-carboxylic acid (21.3 g) in tetrahydrofuran (300 mL) was added 60% sodium hydride (18 g, containing mineral oil) under cooling to 0° C. The reaction mixture was stirred for 30 min under cooling to 0° C. To the reaction mixture was added dropwise 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (46 g) under cooling to 0° C., and the mixture was further stirred at 80° C. for 2 days. Water was added to the reaction mixture under cooling to 0° C., and the mixture was extracted with ethyl acetate. To the aqueous layer was further added 10% hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (32 g).

후처리

  1. temperatureunder cooling to 0° C
  2. temperatureunder cooling to 0° C.
  3. stirringthe mixture was further stirred at 80° C. for 2 days
  4. temperatureunder cooling to 0° C.
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe extract was dried over sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6f0cb7cf409f4b6da26145a8fe848f96
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772277B2

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