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

HRID 478621

Reaktionsgleichung

Reaktionsgleichung von HRID 478621
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]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:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67878Methyl 4-fluorobenzoate

Produkt 1

HCID 1472668Methyl 4-(4-methylpiperazin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Fluorobenzoic acid methyl ester (34 mmol), 1-methyl-piperazine (75 mmol) and potassium carbonate (34 mmol) are suspended in acetonitrile (30 ml) and stirred under reflux for three days. 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 purified by flash chromatography on silica gel with (CH2Cl2/MeOH=95:5) 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 pale yellow powder with mp. 117-119° C., Rf=0.20 (CH2Cl2/MeOH=95:5) is obtained.

Aufarbeitung

  1. temperatureunder reflux for three days
  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. customThe residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=95:5) as mobile phase
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA pale yellow powder with mp. 117-119° C., Rf=0.20 (CH2Cl2/MeOH=95:5) is obtained

Quellen und Nachweise

ORD-Eintrag
ord-f8e68535ffe6496eb0ba31d65120bc69
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642239B2

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