Potassium Carbonate → Methyl 4-(4-ethylpiperazin-1-yl)benzoate

HRID 478624Notes

Reaction equation

HRID 478624 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1.[CH2:12]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:17]2[CH2:18][CH2:19][N:14]([CH2:12][CH3:13])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 791961-Ethylpiperazine

Product 1

HCID 57781922Methyl 4-(4-ethylpiperazin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Fluorobenzoic acid methyl ester (53 mmol), 1-ethyl-piperazine (44 mmol) and potassium carbonate (44 mmol) are suspended in dimethyl-acetamide (50 ml) and stirred under reflux overnight. After evaporation of the solvent, the residue is dissolved in water and extracted three times with ethyl acetate. The extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether/pentane and the solid filtered of and dried (vacuum). A brownish powder with mp. 102-104° C., Rf=0.22 (CH2Cl2MeOH=95:5) is obtained.

Workup

  1. temperatureunder reflux overnight
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe extract is dried over sodium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA brownish powder with mp. 102-104° C., Rf=0.22 (CH2Cl2MeOH=95:5) is obtained

Sources & evidence

ORD record
ord-10a2ca4e7f8a42cb85fa11b1a8b11eec
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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