Phthalimide → 2-[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-ylmethyl]isoindole-1,3-dione

HRID 348756

Reaktionsgleichung

Reaktionsgleichung von HRID 348756
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:20][CH2:21][CH3:22])[C:11]2[CH:17]=[C:16]([CH2:18]O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]1(=[O:55])[NH:49][C:48](=[O:50])[C:47]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]12.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:20][CH2:21][CH3:22])[C:11]2[CH:17]=[C:16]([CH2:18][N:49]3[C:45](=[O:55])[C:46]4[C:47](=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:48]3=[O:50])[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:24][CH3:25]

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 23079221[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-yl]methanolHCID 66777355Diethylazodicarboxylate toluene

Produkt 1

HCID 231555012-[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-ylmethyl]isoindole-1,3-dioneAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound (302 mg) obtained in Example 125-4 was dissolved in toluene (6.0 ml) and added with triphenylphosphine (275 mg) and phthalimide (193 mg), followed by cooling to 0° C. In this solution, a 40% diethyl azodicarboxylate/toluene solution (452 mg) was dropped. After that, the solution was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with water. Then, the solution was subjected to extraction with chloroform and the extract was then washed with saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (174 mg) as a pale-yellow solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water
  5. extractionThen, the solution was subjected to extraction with chloroform
  6. washthe extract was then washed with saturated saline solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b38b06ee95044a93b17e6cf98e20a304
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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