Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)propan-2-amine

Temperature

170 °C

To a solution N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}acetamide (2.0 g, 8.16 mmol) in ethylene glycol (5 mL) was added KOH (3.66 g, 8.16 mmol) and the resulting mixture was heated for 48 h at 170° C. After cooling to rt, the reaction mixture was extracted with Et2O (3×20 mL). The combined organic layers were washed with water (4×), dried over MgSO4, filtered and evaporated to give a colorless oil. This oil was dissolved in Et2O (30 mL) and a saturated solution of HCl in Et2O (10 mL) was added. The white precipitate was collected, washed with Et2O (3×10 mL) and dried under vacuo. This solid was then poured into Et2O (50 mL) and a 1N aqueous solution of NaOH (20 mL) were added. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with water (2×20 mL), dried over MgSO4, filtered and evaporated to give the title compound as colorless oil (1.2 g, 72%). 1H NMR (CDCl3, 300 MHz) δ 7.60-7.46 (m, 4H), 1.53 (br s, 2H), 1.43 (s, 6H). HPLC (Condition A), Rt: 1.73 min (HPLC purity: 94.0%).

1. temperatureAfter cooling to rt
2. extractionthe reaction mixture was extracted with Et2O (3×20 mL)
3. washThe combined organic layers were washed with water (4×)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto give a colorless oil
8. customThe white precipitate was collected
9. washwashed with Et2O (3×10 mL)
10. customdried under vacuo
11. additionThis solid was then poured into Et2O (50 mL)
12. additiona 1N aqueous solution of NaOH (20 mL) were added
13. customThe organic layer was separated
14. extractionthe aqueous layer was extracted with Et2O
15. washThe combined organic layers were washed with water (2×20 mL)
16. dry with materialdried over MgSO4
17. filtrationfiltered
18. customevaporated

ORD record

ord-d6c5941264c348a69ad750301cbece26

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592477B2