Potassium Carbonate → 4-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl ester

HRID 478634Notes

Reaction equation

HRID 478634 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:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:22]2[CH2:23][CH2:24][N:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:20][CH2:21]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 759941-Benzylpiperazine

Product 1

HCID 534068034-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Fluorobenzoic acid methyl ester (200 mmol), 1-benzyl-piperazine (300 mmol), and potassium carbonate (300 mmol) are suspended in acetonitrile (400 ml) and stirred under reflux for 6 days. After evaporation of the solvent, the residue is dissolved in water and extracted three times with diethylether. The extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatographic on silica gel with (CH2Cl2 first, then CH2Cl2/MeOH=15:1) as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether/pentane and the solid filtered of and dried (vacuum). A powder with mp. 105-107° C. is obtained.

Workup

  1. temperatureunder reflux for 6 days
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted three times with diethylether
  5. dry with materialThe extract is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is purified by flash chromatographic on silica gel with (CH2Cl2 first
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA powder with mp. 105-107° C. is obtained

Sources & evidence

ORD record
ord-643943c8625e4bde87b0e059975f3e40
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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