Ethanol → N-Ethyl cyclohexylamine

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.

1. customprepared
2. customthe temperature below 65° C
3. temperatureThe reaction mixture was heated
4. temperatureat reflux temperature for 1½ h
5. additionwas added
6. extractionthe mixture was extracted with diethyl ether (3×250 mL)
7. washThe combined organic phases was washed with brine (150 mL)
8. dry with materialdried over anhydrous magnesium sulphate
9. customevaporated to dryness
10. dissolutionThe residue was dissolved in ethanol (100 mL)
11. customthe solution was evaporated to dryness in vacuo

ORD record

ord-f1a51b5b3fdc44979a6911715be587aa

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582769B2