2,2,2-Trifluoroethylamine hydrochloride → HCID 61392703, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,2,2-trifluoroethylamine hydrochloride (0.271 g) in dichloromethane/water (15/0.5 mL) at 0° C. was added sodium nitrite (0.166 g) and the resulting yellow solution was stirred for 1 hour at 0° C. The reaction mixture was then cooled to −78° C. and 2-o-tolylacetaldehyde (0.134 g) was added, followed by zirconium(IV)tetrachloride. After stirring for 2 hrs at −78° C. cooling was stopped and methanol (3 mL) and saturated solution of NaHCO3 (10 mL) were added. The mixture was extracted with dichloromethane and the extracts were dried and concentrated. Evaporation residue (194 mg) was dissolved in methanol (3 ml) and solution was cooled to 0° C. Sodium borohydride (44 mg) was added and the reaction mixture was stirred for 25 minutes. K2CO3-solution (2M, 5 mL) was added to the reaction mixture, followed by water (5 mL) after 5 min and the resulting solution was extracted with EtOAc. Extracts were dried and concentrated and the residue was purified by separation method E (EtOAc/heptane). (Yield 121 mg).

Provenance & Evidence