Water → 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oxime

HRID 2191143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191143
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14](=O)[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[N:25][OH:26])[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 594381311-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone

Produkt 1

HCID 866440181-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oximeAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2 g (6.1 mmol) 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone, 0.869 g (12.5 mmol) hydroxylamine, hydrochloride and 1.03 g (12.5 mmol) sodium acetate in 25 mL ethanol was heated to reflux for 2 h. After cooling to room temperature water was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a ethyl acetate. The product containing fractions were evaporated to yield 1.6 g (77%) of the title compound as colorless viscous oil. MS (m/e): 343.2 [(M+H)+].

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography on silica eluting with a ethyl acetate
  9. additionThe product containing fractions
  10. customwere evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6cb2a17c345c4adbba99d9ee92b55d06
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324248B2

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