Potassium Carbonate → NSC226270

HRID 454206Notes

Reaction equation

HRID 454206 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].Br[CH2:9][CH2:10][CH2:11][OH:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:12][CH2:11][CH2:10][CH2:9][N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 123083-Bromo-1-propanol

Product 1

HCID 313147NSC226270Yield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of pyrrolidine-2,5-dione (5 g, 50.5 mmol) and 3-bromopropan-1-ol (6.85 ml, 76 mmol) in acetonitrile (80 ml) containing potassium carbonate (14 g, 100 mmol) was refluxed overnight. After cooling, the mixture was filtered and the filtrate was evaporated. The residue was dissolved in methylene chloride and purified by column chromatography, eluting with ethylacetate/petroleum ether (4/1). After evaporation of the volatiles, the residue was distilled at 100-125° C. under about 0.1 mm Hg to give 1-(3-hydroxypropyl)pyrrolidin-2,5-dione (2.6 g, 34%).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in methylene chloride
  6. custompurified by column chromatography
  7. washeluting with ethylacetate/petroleum ether (4/1)
  8. customAfter evaporation of the volatiles
  9. distillationthe residue was distilled at 100-125° C. under about 0.1 mm Hg

Sources & evidence

ORD record
ord-2f464b7069be462eb33bb928d109911c
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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