Potassium Carbonate → HCID 58218898, compound

HRID 1930527Notes

Reaction equation

HRID 1930527 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.F[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12][N:11]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 582188803-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Product 1

HCID 58218898HCID 58218898, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (0.30 g) and 4-fluorobenzonitrile (0.12 g) in DMSO (dimethylsurufoxide) was added potassium carbonate (0.27 g), and the mixture was heated with stirring at 120° C. for 6 hours. The mixture was cooled to room temperature and then poured onto water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]benzonitrile (0.05 g). 1H-NMR (CDCl3) δ: 2.51-2.62 (1H, m), 2.86-2.94 (1H, m), 3.56-3.61 (2H, m), 3.80 (1H, d), 4.12 (1H, d), 6.59 (2H, d), 7.26 (2H, br s), 7.41 (1H, t), 7.52 (2H, d).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. additionpoured onto water, which
  4. extractionwas then extracted twice with ethyl acetate
  5. washwhich was then washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter the drying agent was filtered off
  8. distillationthe solvent was distilled away under the reduced pressure
  9. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-0eb2e81b71a04a1c8144e4790d28327c
Source dataset
uspto-grants-2012_05
Patent number
US08188122B2

Reaction notes

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