Ammonium Acetate → 1-[3-(Trifluoromethoxy)phenyl]ethan-1-amine

Temperature

120 °C

An Emrys Process Vial (2-5 ml) was charged with 420 mg (2 mmol) of 1-(4-trifluoromethoxy-phenyl)-ethanone, ammonium acetate in MeOH (4.0 ml of a 5 M solution, 20 mmol) and sodium cyanoborohydride in MeOH (0.440 ml of a 5 M solution, 2.2 mmol). The reaction vessel was sealed and heated to 120° C. for 5 min in an Emrys Optimizer. After cooling and manual release of remaining pressure the vessel was uncapped and the reaction mixture concentrated at reduced pressure. The residue was dissolved in Et2O (10 ml) and extracted with 2 M aqueous HCl (3×5 ml). The combined aqueous phases were adjusted to pH 9 with a 10 M aqueous KOH and extracted with CH2Cl2 (4×10 ml). The combined organic phases were dried over MgSO4 and the solvent evaporated at reduced pressure to afford 1-(3-trifluoromethoxy-phenyl) -ethyl amine which is used as crude product for step 2.

1. customThe reaction vessel was sealed
2. temperatureAfter cooling
3. concentrationthe reaction mixture concentrated at reduced pressure
4. dissolutionThe residue was dissolved in Et2O (10 ml)
5. extractionextracted with 2 M aqueous HCl (3×5 ml)
6. extractionextracted with CH2Cl2 (4×10 ml)
7. dry with materialThe combined organic phases were dried over MgSO4
8. customthe solvent evaporated at reduced pressure

ORD record

ord-d69cb1d2b7d5445c8ff6a07a2477005b

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638553B2