Potassium Carbonate → 3-bromo-1-methyl-4-(4-oxopiperidin-1-yl)-1H-pyrrole-2,5-dione

HRID 1258295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258295
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[C:6]=1[Br:7].Cl.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>O>[Br:7][C:6]1[C:5](=[O:8])[N:4]([CH3:9])[C:3](=[O:10])[C:2]=1[N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 181552,3-Dibromo-N-methylmaleimideHCID 30848514-Piperidone hydrochloride

Produkt 1

HCID 593547873-bromo-1-methyl-4-(4-oxopiperidin-1-yl)-1H-pyrrole-2,5-dioneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione (100 mg, 0.373 mmol) in AcN (20 mL) was added piperidin-4-one hydrochloride (101 mg, 0.746 mmol) at room temperature followed by K2CO3 (102 mg, 7.46 mol). The reaction mixture was then refluxed for 2 h, diluted with water, extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel column chromatography eluting with 30% EtOAc in hexanes to afford 3-bromo-1-methyl-4-(4-oxopiperidin-1-yl)-1H-pyrrole-2,5-dione (100 mg, 99%) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 2 h
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel column chromatography
  8. washeluting with 30% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-04c1058e35b54ad1be12a0071bfdd575
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466148B2

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