Reaction #595303

Reaction equation

1-(trifluoromethyl)cyclopropanamine

diisopropylethylamine

succinic anhydride

→

4-oxo-4-{[1-(trifluoromethyl)cyclopropyl]amino}butanoic acid

Solvents

dioxane

Conditions

Workup

1. 1
   workup.WAITto stand overnight at this temperature
2. 2
   workup.STIRRINGAgain, stirring
3. 3
   workup.WAITwas continued for 20 min at 80° C.
4. 4
   Temperatureto cool to room temperature
5. 5
   Concentrationthe solution was concentrated
6. 6
   WashRepeatedly, the solution was washed alternately with ethyl acetate and with water
7. 7
   OtherThe combined organic phases were dried
8. 8
   Concentrationconcentrated

Procedure

Slowly, 800.7 mg (4.96 mmol) of 1-(trifluoromethyl)cyclopropanamine and 0.85 ml (4.96 mmol) of diisopropylethylamine were added to a solution of 496 mg (4.96 mmol) of succinic anhydride in 10 ml of dioxane, with ice-cooling (10° C.). Stirring was continued for 20 min at room temperature, and the mixture was allowed to stand overnight at this temperature. Again, stirring was continued for 20 min at 80° C., the mixture was allowed to cool to room temperature, and the solution was concentrated. Repeatedly, the solution was washed alternately with ethyl acetate and with water. The combined organic phases were dried and concentrated. This gave 815.8 mg (73% of theory) of the desired compound.

Source