Ethyl Acetate → 3-[3-(Trifluoromethyl)phenyl]propan-1-amine

Temperature

0 °C

To a solution of 3-(3-trifluoromethyl-phenyl)-propionamide (12) (3.4 g, 15.7 mmol) in THF (70 mL) was added dropwise a solution of lithium aluminum hydride in THF (1.0 M, 15.7 mL, 15.7 mmol) at room temperature. The reaction mixture was heated to reflux for 4 hours, then cooled to 0° C. Ethyl acetate was added to quench the reaction. Sodium hydroxide (5 N) was added and the mixture was refluxed for 30 min. The reaction was cooled to room temperature. Ethyl acetate was added to extract the product. The organic layer was separated and washed by saturated sodium bicarbonate and brine, then dried over MgSO4. Evaporation gave a crude oil, which purified by chromatography to give compound 13 as a colorless oil (1.6 g, 50.2%).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 4 hours
3. customto quench
4. customthe reaction
5. temperaturethe mixture was refluxed for 30 min
6. temperatureThe reaction was cooled to room temperature
7. extractionto extract the product
8. customThe organic layer was separated
9. washwashed by saturated sodium bicarbonate and brine
10. dry with materialdried over MgSO4
11. customEvaporation
12. customgave a crude oil, which
13. custompurified by chromatography

ORD record

ord-831e5adfc7d74a738432e08ae678b14d

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361789B1