3-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)-2-propenyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide → 3-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)propyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide

HRID 35345Notes

Reaction equation

HRID 35345 reaction equation
[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH:11]=[C:12]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7][N:6]([CH2:27][C:28]([NH:30][C:31]2[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:38])=[O:29])[CH2:5]1)=[O:3].[H][H]>[Pd].CO>[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH2:11][CH:12]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7][N:6]([CH2:27][C:28]([NH:30][C:31]2[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:38])=[O:29])[CH2:5]1)=[O:3]

Participants

5

Reactant 2

HCID 545422813-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)-2-propenyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 142302243-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)propyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4 parts of 3-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)-2-propenyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dissolved in acetonitrile. The solution was filtered and the filtrate was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.21 parts of 3-(aminocarbonyl)-4-[3,3-bis(4-fluorophenyl)propyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide; mp. 143.2° C. (compound 170).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. filtrationThe product was filtered off
  8. dissolutiondissolved in acetonitrile
  9. filtrationThe solution was filtered
  10. customthe filtrate was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-ad69b0e3e4624553a779d887e44f7b5b
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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