Acetaldehyde → N-ethyl-N-(trifluoroethyl)amine hydrochloride

Temperature

0 °C

To a solution of 2,2,2-trifluoroethylamine hydrochloride (0.5 g, 3.7 mmol) in MeOH (5 mL) was added triethylamine (0.51 mL, 0.37 mmol) followed by acetaldehyde (1.0 mL, excess). The reaction mixture was then stirred at 0° C. for 3 h. Sodium borohydride (1 g, 5.9 mmol) was then added and the reaction mixture was stirred at 0° C. for 20 min. The reaction was quenched with 1M NaOH (10 mL) and the aqueous layer was extracted with DCM (25 mL). The organic layer was separated and to it was added 2M HCl in Et2O (10 mL). The resultant precipitate was filtered to give 0.45 g of N-ethyl-2,2,2-trifluoroethanamine hydrochloride, (yield: 75%).

1. stirringthe reaction mixture was stirred at 0° C. for 20 min
2. customThe reaction was quenched with 1M NaOH (10 mL)
3. extractionthe aqueous layer was extracted with DCM (25 mL)
4. customThe organic layer was separated and to it
5. additionwas added 2M HCl in Et2O (10 mL)
6. filtrationThe resultant precipitate was filtered

ORD record

ord-57653ee4763c4c8dadf7e43c8a6e9a1d

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133998B2