Water → 4-Phenylcyclohexylamine

HRID 510746

Reaktionsgleichung

Reaktionsgleichung von HRID 510746
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[C:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3438824-Phenylcyclohexanone oximeHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 298974-PhenylcyclohexylamineAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-phenylcyclohexanone oxime (0.310 g, 1.64 mmol) in THF (3 ml) was added 1M lithium aluminum hydride in THF (3.44 ml, 3.44 mmol), and the reaction was heated to reflux for 4 hours. The reaction was allowed to cool to ambient temperature, and water (0.131 ml), 1M NaOH (0.131 ml) and additional water (0.393 ml) were added, and the reaction was stirred for 30 minutes. The reaction was diluted with EtOAc and filtered. The filtrate was concentrated to yield 100 mg of the title compound (34.8% yield) as a 1:1 mixture of cis and trans isomers.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-da9c3c97fdf146a692d6518fe4b57949
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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