Potassium Carbonate → Methyl 4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)-benzoate

HRID 2039981Notes

Reaction equation

HRID 2039981 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[C:13]([F:16])([F:15])[F:14].[CH3:17][N:18]([CH3:24])[CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:17][N:18]([CH3:24])[CH:19]1[CH2:23][CH2:22][N:21]([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[C:13]([F:16])([F:15])[F:14])[CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27585193-(Dimethylamino)pyrrolidineHCID 57443327Methyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

Product 1

HCID 68756607Methyl 4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)-benzoateYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reactor is charged with 1.2 g (4.06 mmol) of the compound obtained in step 2, 0.55 g (4.88 mmol) of 3-dimethylaminopyrrolidine, 2.8 g (20.3 mmol) of potassium carbonate and 25 ml acetone. The mixture is heated for 6 hours at reflux. The solvent is evaporated under reduced pressure and 100 ml of water is then added. The obtained solution is extracted with 3*30 ml ethyl acetate. The organic phases are combined, dried on sodium sulphate and then evaporated under reduced pressure to give the expected product (0.8 g, 61%),

Workup

  1. temperatureThe mixture is heated for 6 hours
  2. temperatureat reflux
  3. customThe solvent is evaporated under reduced pressure and 100 ml of water
  4. additionis then added
  5. extractionThe obtained solution is extracted with 3*30 ml ethyl acetate
  6. customdried on sodium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c1bee9a872e64e41a8538ae814337eef
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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