2-(1-Cyclohexenyl)ethylamine → [2-(Cyclohex-1-en-1-yl)ethyl](methyl)amine

To a solution of 2-(1-cyclohexenyl)ethylamine (4.0 g) in 1,4-dioxane (40 mL) was added di-tert-butyldicarbonate (7.7 g). After gas evolution ceased (≈2 h) the reaction was concentrated. A portion of the residue (2 g) was dissolved in THF (10 mL) followed by addition of LiAlH4 (10 mL, 1M THF), which caused an exotherm. After 3 h, more LiAlH4 solution was added (4 mL), and the reaction was warmed to reflux. After 1 h, the reaction was cooled, and quenched cautiously with vigorous stirring by the addition of water (0.57 mL), 1M NaOH (0.6 mL), and more water (1.5 mL). The suspension was filtered through celite, which was washed with ether. The organic solution was concentrated to give the desired product as a volatile oil (0.8 g).

1. custom(≈2 h)
2. concentrationwas concentrated
3. dissolutionA portion of the residue (2 g) was dissolved in THF (10 mL)
4. additionfollowed by addition of LiAlH4 (10 mL, 1M THF), which
5. additionmore LiAlH4 solution was added (4 mL)
6. temperaturethe reaction was warmed to reflux
7. waitAfter 1 h
8. temperaturethe reaction was cooled
9. customquenched cautiously
10. filtrationThe suspension was filtered through celite, which
11. washwas washed with ether
12. concentrationThe organic solution was concentrated

ORD record

ord-7f058490acaa40edb293e6929fcdbcd0

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310095B1