1,4-Dibromobutane → 1-(4-Bromobutyl)pyrrolidin-2-one

HRID 1646482Notes

Reaction equation

HRID 1646482 reaction equation
[OH-].[K+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13]Br>O1CCCC1.[Br-].C([N+](CC)(CC)CC)C>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 120252-PyrrolidoneHCID 14797Potassium Hydroxide

Product 1

HCID 152878411-(4-Bromobutyl)pyrrolidin-2-oneYield 38.8%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 37 g of powdered KOH in 500 ml of tetrahydrofuran (THF) were added 25.2 g of tetraethylammonium bromide. Then, a solution of 51.6 g of 2-pyrrolidinone and 129.6 g of 1,4-dibromobutane in 100 ml of THF was added dropwise to the mixture. The mixture was heated and refluxed for 2 hours. The precipitate was filtered, and the THF evaporated. The residue was dissolved in dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue distilled to yield 51.2 g of 1-(4-bromobutyl)-2-pyrrolidinone (38.8% yield) having a boiling point of 120° C. at 0.05 mm Hg.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 2 hours
  3. filtrationThe precipitate was filtered
  4. customthe THF evaporated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. distillationthe residue distilled

Sources & evidence

ORD record
ord-c6cd0210a95e4aab8392400e8d919f73
Source dataset
uspto-grants-1993_01
Patent number
US05180726

Reaction notes

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