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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1949075
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

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

Produkt 1

HCID 581293421-Benzyl-4-hydroxy-piperidine-4-carboxylic acid methyl-(4-trifluoromethoxy-phenyl)-amideAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516920Potassium bisulfateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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)+].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f4b901d5562748b393dd6ee6125e385d
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399676B2

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