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Potassium Hydroxide → 1-Benzyl-4-hydroxy-piperidine-4-carboxylic acid methyl-(4-trifluoromethoxy-phenyl)-amide

HRID 1949075
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인쇄 미리보기

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HRID 1949075 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:29]C(=O)C)([C:14](=[O:28])[N:15]([CH3:27])[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>OS([O-])(=O)=O.[K+]>[CH3:27][N:15]([C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=1)[C:14]([C:11]1([OH:29])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)=[O:28]
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참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 58129329Acetic acid 1-benzyl-4-[methyl-(4-trifluoromethoxy-phenyl)-carbamoyl]-piperidin-4-yl ester

생성물 1

HCID 581293421-Benzyl-4-hydroxy-piperidine-4-carboxylic acid methyl-(4-trifluoromethoxy-phenyl)-amide수율 59.1%

시약·촉매·용매 1

HCID 516920Potassium bisulfate용매

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온도
70 °C

실험 절차

A mixture of 0.782 g (1.7 mmol) acetic acid 1-benzyl-4-[methyl-(4-trifluoromethoxy-phenyl)-carbamoyl]-piperidin-4-yl ester and excess KOH 5M was heated to 70° C. The mixture was diluted with KHSO4 1N aq. and extracted with ethyl acetate. the combined organic fractions were dried with MgSO4 and evaporated. The residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and HCOOH. The product containing fractions were evaporated to yield 0.41 g (58%) of the title compound. MS (m/e): 409.1 [(M+H)+].

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic fractions were dried with MgSO4
  3. customevaporated
  4. customThe residue was purified by preparative HPLC on reversed phase
  5. washeluting with a gradient
  6. customformed from acetonitrile, water and HCOOH
  7. additionThe product containing fractions
  8. customwere evaporated

출처 및 근거

ORD 기록
ord-f4b901d5562748b393dd6ee6125e385d
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399676B2

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