Hydrochloric Acid → 3-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamide

HRID 35334Notes

Reaction equation

HRID 35334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:24])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]2C(C)(C)[NH:19][C:20](=[O:21])[CH:14]2[CH2:13]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:19][C:20]([CH:14]1[NH:15][CH2:16][CH2:17][N:12]([CH2:11][C:10]([NH:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[O:24])[CH2:13]1)=[O:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14230252N-(2,6-dichlorophenyl)hexahydro-3,3-dimethyl-1-oxoimidazo[1,5-a]pyrazine-7(1H)-acetamide

Product 1

HCID 142302313-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamideYield 64%

Procedure

A mixture of 23.8 parts of N-(2,6-dichlorophenyl)hexahydro-3,3-dimethyl-1-oxoimidazo[1,5-a]pyrazine-7(8H)-acetamide and 256 parts of a hydrochloric acid solution 0.5N was stirred and refluxed for 2 hours. The reaction mixture was cooled overnight to room temperature, alkalized and salted out with sodium carbonate. The product was extracted with trichloromethane. The extract was filtered and the filtrate was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 13.6 parts (64%) of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide; mp. 180.4°-182.8° C. (intermediate 125).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled overnight to room temperature
  3. extractionThe product was extracted with trichloromethane
  4. filtrationThe extract was filtered
  5. customthe filtrate was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-62e55a7766674b6b9bc1d54ee3250175
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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