Potassium Carbonate → 2-(4-(4-Diphenylmethyl-piperazin-1-yl)-3-hydroxy-butyl]isoindolin-1,3-dione

HRID 1070756

Reaction equation

HRID 1070756 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[CH:17]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:24]1([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:30]2[CH2:31][CH2:32][N:33]([CH2:16][CH:2]([OH:1])[CH2:3][CH2:4][N:5]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6]3=[O:15])[CH2:34][CH2:35]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 3394332-[2-(oxiran-2-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 223976852-(4-(4-Diphenylmethyl-piperazin-1-yl)-3-hydroxy-butyl]isoindolin-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (˜25 mmol) 2-(3,4-epoxybutyl)-isoindolin-1,3-dione, 7.5 g (30 mmol) benzhydrylpiperazine and 3.5 g (25 mmol) potassium carbonate are stirred in DMF for 6 hours 80° C. After cooling, the reaction mixture is filtered and concentrated under vacuum. The residue is taken up in 300 ml acetic acid ethyl ester and washed three times each with 20 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationconcentrated under vacuum
  4. washwashed three times each with 20 ml water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under vacuum
  7. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH

Sources & evidence

ORD record
ord-74029f5adc144f849d7c7dffec248640
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Linked notes

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