Potassium Carbonate → ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoate

HRID 1796784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796784
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]([F:49])([F:48])[CH2:27][NH:28][C:29]([C:31]1([CH2:44][CH2:45][CH2:46]Br)[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:30]>CN(C=O)C.C(OCC)(=O)C>[F:25][C:26]([F:48])([F:49])[CH2:27][NH:28][C:29]([C:31]1([CH2:44][CH2:45][CH2:46][N:16]2[CH2:15][CH2:14][N:13]([C:10]3[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=3)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17]2)[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:30]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 105977593-[9-(2,2,2-Trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl bromideHCID 69591845Ethyl 2-methyl-5-piperazinylbenzoate

Produkt 1

HCID 22180176ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoateAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Ethyl 2-methyl-5-piperazinylbenzoate (1.8 g, 9.1 mmol) was dissolved in 20 ml of anhydrous DMF. Potassium carbonate (1.7 g) and 3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl bromide (2.5 g, 6.1 mmol) were added to the solution, and the mixture was stirred at 75° C. for 7 hr. The temperature of the reaction solution was returned to room temperature, and the reaction solution was then diluted with ethyl acetate. The dilution was washed twice with water and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography (development system, n-hexane:ethyl acetate=2:1) to give 2.1 g (yield 59%) of ethyl 5-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazinyl]-2-methylbenzoate as a pale yellow foam.

Aufarbeitung

  1. customwas returned to room temperature
  2. washThe dilution was washed twice with water
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography (development system, n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-99d843331a1d42cf9c242084d7500704
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030120B2

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