Hydrochloric Acid → 2-{4-[(4-Dipropylaminobutyl amino)-methyl]benzyl}isoindole-1,3-dione

HRID 1173863Notes

Reaction equation

HRID 1173863 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.Cl.[CH2:22]([N:25]([CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH2:23][CH3:24].S([O-])([O-])(=O)=O.[Mg+2]>CO.C(N(CC)CC)C>[CH2:31]([N:25]([CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:14][CH:15]=1)[CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 7138396N,N-dipropylbutane-1,4-diamineHCID 231555474-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)benzaldehyde

Product 1

HCID 231554302-{4-[(4-Dipropylaminobutyl amino)-methyl]benzyl}isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

The compound (103 mg) obtained in Example 25-1 was dissolved in anhydrous methanol (10 ml) and then added with the hydrochloride (114 mg) of the compound obtained in Example 1-2. Then, the solution was added with triethylamine (0.108 ml) and anhydrous magnesium sulfate (3 g), followed by stirring at room temperature for 1 hour. Anhydrous magnesium sulfate was removed from the solution by Celite filtration. Then, methanol was distilled off and the residue was dried using a vacuum pump. The residue was dissolved in anhydrous methanol (10 ml) and sodium borohydride (22.0 mg) was then gradually added under ice-cooling. The solution was warmed to room temperature and then stirred for 1 hour. After completion of the reaction, methanol was distilled off and the residue was then added with water and chloroform to extract the organic layer. After the organic layer had been dried with anhydrous sodium sulfate, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (60.3 mg) as a pale-yellow viscous liquid.

Workup

  1. customAnhydrous magnesium sulfate was removed from the solution by Celite filtration
  2. distillationThen, methanol was distilled off
  3. customthe residue was dried
  4. dissolutionThe residue was dissolved in anhydrous methanol (10 ml)
  5. additionsodium borohydride (22.0 mg) was then gradually added under ice-
  6. temperaturecooling
  7. temperatureThe solution was warmed to room temperature
  8. stirringstirred for 1 hour
  9. customAfter completion of the reaction, methanol
  10. distillationwas distilled off
  11. additionthe residue was then added with water and chloroform
  12. extractionto extract the organic layer
  13. dry with materialAfter the organic layer had been dried with anhydrous sodium sulfate
  14. distillationthe solvent was distilled off
  15. customthe residue was then purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-ed10a393456b424384124558fbc3f08a
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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