Sodium Carbonate → N-(2-acetylphenyl)-3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)-4-pentenyl]-1-piperazineacetamide

HRID 1638645Notes

Reaction equation

HRID 1638645 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31](=[O:42])[CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH:35]([C:39]([NH2:41])=[O:40])[CH2:34]1)(=[O:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31](=[O:42])[CH2:32][N:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[CH:35]([C:39]([NH2:41])=[O:40])[CH2:34]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 147225505-Bromo-1,1-bis-(4-fluorophenyl)pent-1-eneHCID 15087723N-(2-acetylphenyl)-3-(aminocarbonyl)-1-piperazineacetamide

Product 1

HCID 14722670N-(2-acetylphenyl)-3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)-4-pentenyl]-1-piperazineacetamideYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.86 parts of 1,1'-(5-bromo-1-penten-1-ylidene)bis-[4-fluorobenzene], 1.50 parts of N-(2-acetylphenyl)-3-(aminocarbonyl)-1-piperazineacetamide, 0.80 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred for 20 hours at 80° C. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 2.07 parts (73.9%) of N-(2-acetylphenyl)-3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)-4-pentenyl]-1-piperazineacetamide; mp. 110.7° C. (compound 18).

Workup

  1. customThe reaction mixture was evaporated
  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 by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-76da526a6044499c8c78fd868b7d7de5
Source dataset
uspto-grants-1989_11
Patent number
US04880808

Reaction notes

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