Hydrochloric Acid → 2-Ethylcyclohexan-1-amine

Temperature

110 °C

To the solution of 2-ethyl-1-(hydroxyimino)cyclohexane (6.8 g, 48.5 mmol) in ethanol (75 mL) were added sodium pieces (about 8.0 g) in portions, and the reaction was heated to reflux at 110° C. overnight. More sodium pieces were added, and the reaction was stirred for another 6 hours. The reaction was treated with concentrated HCl (12 M, 4.0 mL) in water (25 mL). Ethanol was removed in vacuo. The aqueous layer was washed with ether (10 mL), and treated with aqueous KOH (25 mL) and extracted with ether (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to give 2-ethylcyclohexylamine as an off-white oil.

1. temperaturethe reaction was heated
2. customEthanol was removed in vacuo
3. washThe aqueous layer was washed with ether (10 mL)
4. additiontreated with aqueous KOH (25 mL)
5. extractionextracted with ether (3×20 mL)
6. washThe combined organic extracts were washed with brine (20 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-9b755afaf4c2491d9fdf95ef02f48bd0

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06638927B2