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

HRID 2080717Notes

Reaction equation

HRID 2080717 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 231555012-[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-ylmethyl]isoindole-1,3-dioneYield 41.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

The compound (302 mg) obtained in Example 3-4 was dissolved in toluene (6.0 ml) and added with triphenylphosphine (275 mg) and phthalimide (193 mg) and the whole was cooled to 0° C. In this solution, a 40% diethyl azodicarboxylate/toluene solution (452 mg) was dropped and the whole 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 resultant was subjected to extraction with chloroform and washed with a 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.

Workup

  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 resultant was subjected to extraction with chloroform
  6. washwashed with a 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)

Sources & evidence

ORD record
ord-f52d658f4c0e43438fc71d5d16f271a5
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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