3-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamide → 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-(4-oxo-5,5-diphenylpentyl)-1-piperazineacetamide monohydrate

HRID 35346Notes

Reaction equation

HRID 35346 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:20][C:21]([CH:23]1[NH:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]([NH:32][C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[O:31])[CH2:24]1)=[O:22]>CN(C)C=O>[OH2:19].[NH2:20][C:21]([CH:23]1[N:28]([CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:27][CH2:26][N:25]([CH2:29][C:30]([NH:32][C:33]2[C:34]([Cl:40])=[CH:35][CH:36]=[CH:37][C:38]=2[Cl:39])=[O:31])[CH2:24]1)=[O:22]

Participants

4

Reactant 2

HCID 142302313-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamideHCID 19883512HCID 19883512, compound

Product 1

HCID 704188893-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-(4-oxo-5,5-diphenylpentyl)-1-piperazineacetamide monohydrateYield 3.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.45 parts of 5-chloro-1,1-diphenyl-2-pentanone, 9.94 parts of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide and 90 parts of N,N-dimethylformamide was stirred for 48 hours at 60° C. and evaporated. The residue was taken up in water and alkalized with ammonia. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified twice by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in 2,2'-oxybispropane and allowed to stand for 10 days. The product was filtered off and dried at the air, yielding 0.32 parts (3.7%) of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-(4-oxo-5,5-diphenylpentyl)-1-piperazineacetamide monohydrate; mp. 91.6° C. (compound 171).

Workup

  1. customevaporated
  2. extractionThe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified twice by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. waitto stand for 10 days
  12. filtrationThe product was filtered off
  13. customdried at the air

Sources & evidence

ORD record
ord-d98683e2948f4541af6f840083158bae
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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