4-Piperidone → 1-[(2,6-Dimethylphenyl)aminocarbonylmethyl]-4-piperidone

HRID 615378Notes

Reaction equation

HRID 615378 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([CH2:12]Cl)=[O:11].[NH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([CH2:12][N:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 337214-PiperidoneHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 133933531-[(2,6-Dimethylphenyl)aminocarbonylmethyl]-4-piperidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude [(2,6-dimethylphenyl)aminocarbonylmethyl]chloride, prepared in Preparation B (50 g., 0.25 moles) and 4-piperidone (86 g, 1 mole) are dissolved in 500 ml of ethanol. The mixture is refluxed for two hours, and then cooled and evaporated. The product is recovered by adding aqueous ammonia to the residue, and extracting with methylene chloride. Three portions of methylene chloride are used, which are collected, washed with water, and evaporated to a semi-solid. Upon addition of diethylether, the product crystallizes and is filtered. The resulting crude mixture is boiled with ether and then evaporated to a residue and triturated with hexane to yield pure material, 1-[(2,6-dimethylphenyl)aminocarbonylmethyl]-4-piperidone. This material is of sufficient purity for use in Reaction Sequences 2 to 5.

Workup

  1. temperatureThe mixture is refluxed for two hours
  2. temperaturecooled
  3. customevaporated
  4. customThe product is recovered
  5. additionby adding aqueous ammonia to the residue
  6. extractionextracting with methylene chloride
  7. customwhich are collected
  8. washwashed with water
  9. customevaporated to a semi-solid
  10. additionUpon addition of diethylether
  11. customthe product crystallizes
  12. filtrationis filtered
  13. customevaporated to a residue
  14. customtriturated with hexane

Sources & evidence

ORD record
ord-0839b93d1c3545e9a57da228cce56959
Source dataset
uspto-grants-1985_02
Patent number
US04499100

Reaction notes

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