Ethyl Acetate → 4-(2,2,2-Trifluoroethyl)piperazin-1-amine

To a suspension of lithium aluminum hydride (2.22 g, 58.5 mmol) in tetrahydrofuran (100 mL) that cooled with ice bath, a solution of 1-nitroso-4-(2,2,2-trifluoroethyl)piperazine (5.43 g, 27.5 mmol) in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was allowed to warm to ambient temperature, then stirred for 5 days. The reaction mixture was cooled with ice bath, ethyl acetate was added until cease bubbling up, and water (2.1 mL) was added then the mixture was stirred for 20 min. To this mixture, 15% w/v sodium hydroxide solution (2.1 mL) and water (6.3 mL) were added, then the suspension mixture was allowed to warm to ambient temperature and then the mixture was stirred vigorously for 1 h. Magnesium sulfate was added to the mixture and stirred for a while, then the suspension was filtered. The filtrate was concentrated to afford 4-(2,2,2-trifluoroethyl)piperazine-1-amine as oil (4.72 g, y. 94%).

1. temperaturecooled with ice bath
2. temperatureThe reaction mixture was cooled with ice bath
3. customuntil cease bubbling up
4. additionwater (2.1 mL) was added
5. stirringthe mixture was stirred for 20 min
6. additionwere added
7. temperatureto warm to ambient temperature
8. stirringthe mixture was stirred vigorously for 1 h
9. additionMagnesium sulfate was added to the mixture
10. stirringstirred for a while
11. filtrationthe suspension was filtered
12. concentrationThe filtrate was concentrated

ORD record

ord-d98f1df323364e75903cb85e4bdd98fd

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742113B2