Reaction #1005945

Reaction equation

sodium carbonate

t-butyl {4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-2-(trifluoromethyl)benzyl}carbamate

hydrochloric acid

ethanol

→

title compound

Yield 105.6%

1-{4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-2-(trifluoromethyl)phenyl}methanamine

Yield 105.6%

Solvents

ethyl acetate

water

Conditions

Workup

1. 1
   workup.ADDITIONthe reaction solution was diluted
2. 2
   ExtractionAfter the extraction
3. 3
   Washthe organic layer was washed with saturated brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   OtherThe solvent was evaporated off under reduced pressure

Procedure

A mixture comprising t-butyl {4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-2-(trifluoromethyl)benzyl}carbamate (6.0 g), concentrated hydrochloric acid (20 mL) and ethanol (100 mL) was stirred at 50° C. for three hours. After cooling the mixture to room temperature, the reaction solution was diluted by adding water (150 mL) and ethyl acetate (150 mL). By adding sodium carbonate in small portions, the solution was neutralized. After the extraction using ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure to obtain the title compound (5.2 g).

Source