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

HRID 2080708Notes

Reaction equation

HRID 2080708 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 1-1 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 filtration through Celite. Then, methanol was distilled off and the resultant was dried using a vacuum pump. The resultant was dissolved in anhydrous methanol (10 ml) and gradually added with sodium borohydride (22.0 mg) under ice-cooling. The solution was warmed back 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 was 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 filtration through Celite
  2. distillationThen, methanol was distilled off
  3. customthe resultant was dried
  4. dissolutionThe resultant was dissolved in anhydrous methanol (10 ml)
  5. additiongradually added with sodium borohydride (22.0 mg) under ice-
  6. temperaturecooling
  7. temperatureThe solution was warmed back 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 was 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-126462ed264244cebb8fcae13ad3e18f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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