Piperazine → Cvt-2738

HRID 1285541Notes

Reaction equation

HRID 1285541 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][NH:17][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][NH:17][CH2:16][CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 2608606Cvt-2738

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude [(2,6-dimethylphenyl)aminocarbonylmethyl]chloride, prepared in Preparation B (50 g, 0.25 mole) and piperazine (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 harvested 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 ether, 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]piperazine. This material is of sufficient purity for use in Reaction Sequences 1 or 2.

Workup

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

Sources & evidence

ORD record
ord-cfb029ebf5c64436916d51c22de20f9d
Source dataset
uspto-grants-1986_01
Patent number
US04567264

Reaction notes

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