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

HRID 1425834Notes

Reaction equation

HRID 1425834 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5273271e281a4b84a9b63706ad0f8616
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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