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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence