Reaction #1005944

ord-2833baeb11584e4787c4da4f052e18c2

Reaction equation

FC(F)(F)C1(c2cc(Cl)cc(Cl)c2)CCNC1
3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine
N#Cc1ccc(F)cc1C(F)(F)F
4-fluoro-2-trifluoromethylbenzonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
N,N-dimethylformamide
N#Cc1ccc(N2CCC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)cc1C(F)(F)F
title compound
Yield 42.5%
N#Cc1ccc(N2CCC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)cc1C(F)(F)F
4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-(trifluoromethyl)-benzonitrile
Yield 42.5%

Conditions

Temperature
110°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling the mixture to room temperature
  2. 2
    Washwashed with water three times
  3. 3
    DryingThe organic layer was dried over anhydrous magnesium sulfate
  4. 4
    OtherThe solvent was evaporated off under reduced pressure
  5. 5
    Otherthe residue was then purified by a column chromatography

Procedure

3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (5.6 g), 4-fluoro-2-trifluoromethylbenzonitrile (4.5 g) and potassium carbonate (5.4 g) were added to N,N-dimethylformamide (50 mL), and the mixture was stirred at 110° C. for 4 hours. After cooling the mixture to room temperature, the solution was diluted with ethyl acetate and washed with water three times. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a column chromatography to obtain the title compound (3.8 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09271499B2uspto-grants-2016_03