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Acetic Acid → 2-{4-[(4-Dipropylaminomethylphenylamino)methyl]benzyl}isoindole-1,3-dione

HRID 348633
Notes
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Reaction equation

HRID 348633 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[CH2:21]([N:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23].C([BH3-])#N.[Na+].C(O)(=O)C>CO.O>[CH2:21]([N:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][CH2:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])=[CH:20][CH:19]=2)=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 167770114-Dipropylaminomethyl-anilineHCID 231555474-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)benzaldehyde

Product 1

HCID 210843762-{4-[(4-Dipropylaminomethylphenylamino)methyl]benzyl}isoindole-1,3-dioneYield 250.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound (17.6 mg) obtained in Example 25-1, the compound (13.2 mg) obtained in Example 19-2, and sodium cyanoborohydride (8.7 mg) were dissolved in anhydrous methanol (1.0 ml). The solution was then adjusted to pH 5 with the addition of acetic acid, followed by stirring at room temperature for 4 hours. The reaction solution was added with distilled water and then subjected to extraction with chloroform. After that, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel preparative thin-layer chromatography (chloroform/methanol), thereby obtaining the subject compound (72.9 mg) as a yellow solid.

Workup

  1. extractionsubjected to extraction with chloroform
  2. washAfter that, the organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified through silica gel preparative thin-layer chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9d2746151dc14339af43c58ff20d3f08
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes