Potassium Carbonate → Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate

HRID 16823

Reaktionsgleichung

Reaktionsgleichung von HRID 16823
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:13]1([N:17]2[CH2:22][CH2:21][N:20]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 47386021-Cyclobutylpiperazine

Produkt 1

HCID 57440408Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl 4-fluorobenzoate (0.753 g, 4.48 mmol) was added to a solution of 1-cyclobutylpiperazine (0.571 g, 4.07 mmol) and potassium carbonate (0.563 g, 4.07 mmol) in DMSO (8 mL) under nitrogen. The resulting solution was stirred at 100° C. for 18 h and evaporated to dryness. The residue was triturated with diethyl ether, filtered, and evaporated and the crude product was purified by silica column chromatography, eluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate (0.387 g, 32.9%) as a white solid.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. customevaporated
  5. customthe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4a50fabbb59a43498f3a1e1ac535a4bc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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