Formaldehyde → 1-(4-Chlorophenyl)-3-methylene-2-pyrrolidinone

HRID 1268375Notes

Reaction equation

HRID 1268375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13](O)=O)[C:9]2=[O:16])=[CH:4][CH:3]=1.C=O.COC1CCNCC1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C:10](=[CH2:13])[C:9]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 776664-MethoxypiperidineHCID 40570841-(4-Chlorophenyl)-2-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 185444121-(4-Chlorophenyl)-3-methylene-2-pyrrolidinoneYield 62.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.56 g of 1-(4-chlorophenyl)-3-carboxy-2-pyrrolidinone was mixed with 7 ml of methanol. Thereto were added 0.26 g of 75% paraformaldehyde and 0.75 g of 4-methoxypiperidine. The mixture was refluxed for 2 hours. The reaction mixture was concentrated to dryness. The residue was purified by silica gel column chromatography using chloroform (a solvent) to obtain 0.85 g of 1-(4-chlorophenyl)-3-methylene-2-pyrrolidinone.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2dee16d260f4c7f86b8b0d451a7f180
Source dataset
uspto-grants-2003_04
Patent number
US06555694B1

Reaction notes

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