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Dimethylformamide → [1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 1647048
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HRID 1647048 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Br[CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C:18]([CH:20]2[CH2:25][CH2:24][N:23]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1
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참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidine

생성물 1

HCID 10917690[1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

시약·촉매·용매 3

HCID 962
Water
용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

To a stirred, room temperature, mixture of [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone, mono (trifluoroacetate) (1.82 g, 4.03×10-3 mole), potassium carbonate (1.39 g, 1.00×10-2 mole), and sieve dry DMF (15 ml) was added 1-(2-bromoethyl)-4-methoxybenzene (0.87 g, 4.04×10-3 mole). The reaction was then immersed in an oil bath which had been preheated to ca. 90° C. After being stirred at between 80-90° C. for 22 hours, the reaction was allowed to cool to room temperature. The reaction was poured into a separatory funnel containing H2O and a 2:1 mixture of ethyl acetate:toluene. The two phases were mixed and the aqueous layer was separated. The organic layer was washed two times with H2O and once with saturated aqueous NaCl before being dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving an oil which was purified by flash chromatography (ethyl acetate). Crystallization from cyclohexane afforded [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone as off white matted needles: 1.08 g (57%). This material was spectroscopically identical with the previously described product of Example III.

후처리

  1. customThe reaction was then immersed in an oil bath
  2. customhad been preheated to ca. 90° C
  3. temperatureto cool to room temperature
  4. additionThe reaction was poured into a separatory funnel
  5. additionThe two phases were mixed
  6. customthe aqueous layer was separated
  7. washThe organic layer was washed two times with H2O
  8. dry with materialonce with saturated aqueous NaCl before being dried over anhydrous Na2SO4
  9. customThe drying agent was removed by filtration
  10. customthe filtrate was evaporated at reduced pressure
  11. customleaving an oil which
  12. customwas purified by flash chromatography (ethyl acetate)
  13. customCrystallization from cyclohexane

출처 및 근거

ORD 기록
ord-934025c553bb4e5b92cda5bca843f8b7
출처 데이터셋
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05182399

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