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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1647048
[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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Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-934025c553bb4e5b92cda5bca843f8b7
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05182399

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