Reaktion #818608

Reaktionsgleichung

ethanol

water

ethanol

Sodium

4-ethylcyclohexanone oxime

→

ethylcyclohexylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Sonstigethe temperature below 65° C
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturat reflux temperature for 1½ h
5. 5
   workup.ADDITIONwas added
6. 6
   Extraktionthe mixture was extracted with diethyl ether (3×250 mL)
7. 7
   WaschenThe combined organic phases was washed with brine (150 mL)
8. 8
   Trocknendried over anhydrous magnesium sulphate
9. 9
   Sonstigeevaporated to dryness
10. 10
    workup.DISSOLUTIONThe residue was dissolved in ethanol (100 mL)
11. 11
    Sonstigethe solution was evaporated to dryness in vacuo

Vorschrift

Sodium (45 g, 1.96 mol) was slowly added to a solution of 4-ethylcyclohexanone oxime (33 g, 0.23 mol) (prepared according to lit. R. O. Hutchins et al. J. Org. Chem. 60 (1995) 7396-7405)) in 99.9% ethanol (500 mL) while keeping the temperature below 65° C. The reaction mixture was heated at reflux temperature for 1½ h and then stirred at room temperature for further 16 h. A mixture of water (500 mL) and ethanol (100 mL) was added and the mixture was extracted with diethyl ether (3×250 mL). The combined organic phases was washed with brine (150 mL), dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was dissolved in ethanol (100 mL), pH was adjusted to approx. 3 with 4 N hydrochloric acid (60 mL) and the solution was evaporated to dryness in vacuo to give crude ethylcyclohexylamine. The product was purified by recrystallization from ethanol/acetonitrile (4:1) to give 4-trans-ethylcyclohexylamine, hydrochloride as white crystalls.

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