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

HRID 1073189
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HRID 1073189 반응식
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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a1981ee30ff749f9a0722b35d02ef495
출처 데이터셋
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04968684

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