Benzyl Bromide → 1-Benzyl-3-pyrrolidone

HRID 1682002Notes

Reaction equation

HRID 1682002 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.C(OCC)(=O)C>[CH2:9]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 120252-PyrrolidoneHCID 24758Sodium hydride

Product 1

HCID 791761-Benzyl-3-pyrrolidone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

14.4 g (0.33 mol) of 50% sodium hydride dispersion in oil are added in batches to 25.5 g (0.3 mol) of 2-pyrrolidone in 300 ml of absolute dimethylsulphoxide. The mixture is then stirred for 5 hours at 40° to 50° C. and at 25°-30° C. 56.4 g=39.2 ml (0.33 mol) of benzyl bromide are added dropwize. After stirring for 10 hours at ambient temperature the reaction mixture is dissolved in 500 ml of ethyl acetate and extracted several times with water. The organic phase is separated off, dried over magnesium sulphate and the solvent is eliminated in vacuo. The residue obtained is purified over 900 g of aluminium oxide (neutral, activity II) with methylene chloride and 0.1% ethanol. Yield: 35.6 g (67.7% of theory), Rf value: 0.77 (aluminium oxide, neutral, eluant: 5% ethanol in methylene chloride).

Workup

  1. stirringAfter stirring for 10 hours at ambient temperature the reaction mixture
  2. extractionextracted several times with water
  3. customThe organic phase is separated off
  4. dry with materialdried over magnesium sulphate
  5. customThe residue obtained
  6. customis purified over 900 g of aluminium oxide (neutral, activity II) with methylene chloride and 0.1% ethanol

Sources & evidence

ORD record
ord-b2a59a06d2d7492aa3a954e546a5732f
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

Loading…