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

HRID 655413

Reaction equation

HRID 655413 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-bb8319acfbac470f91d2af378121b2e2
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Linked notes

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