Potassium Carbonate → Ethyl 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoate

HRID 468812Notes

Reaction equation

HRID 468812 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]=1[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]=2[C:21]([F:22])([F:24])[F:23])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 23073576Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

Product 1

HCID 23145917Ethyl 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-methylpiperazine (600 mg, 1.5 mmol), ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate (310 mg, 1.0 mmol), and potassium carbonate (276 mg, 2.0 mmol) in N,N-dimethylformamide (8 mL) were stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried and concentrated to give the product without further purification (600 mg, 72%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customto give the product
  7. customwithout further purification (600 mg, 72%)

Sources & evidence

ORD record
ord-5ddc23fffd004a28a55d26a9a7c0e239
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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