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

HRID 2080862Notes

Reaction equation

HRID 2080862 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 added with the hydrochloride (114 mg) of the compound obtained in Example 1-2. The solution was added with triethylamine (0.108 ml) and anhydrous magnesium sulfate (3 g) and the whole was stirred at room temperature for 1 hour. The solution was subjected to filtration through Celite to remove anhydrous magnesium sulfate and methanol was distilled off, followed by drying with a vacuum pump. The resultant was dissolved in anhydrous methanol (10 ml) and sodium borohydride (22.0 mg) was gradually added thereto under ice-cooling. The solution was warmed back to room temperature and stirred for 1 hour. After completion of the reaction, methanol was distilled off. The resultant was added with water and chloroform and the organic layer was extracted. The resultant was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was 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. filtrationThe solution was subjected to filtration through Celite
  2. customto remove anhydrous magnesium sulfate and methanol
  3. distillationwas distilled off
  4. customby drying with a vacuum pump
  5. dissolutionThe resultant was dissolved in anhydrous methanol (10 ml)
  6. additionsodium borohydride (22.0 mg) was gradually added
  7. temperatureunder ice-cooling
  8. temperatureThe solution was warmed back to room temperature
  9. stirringstirred for 1 hour
  10. customAfter completion of the reaction, methanol
  11. distillationwas distilled off
  12. additionThe resultant was added with water and chloroform
  13. extractionthe organic layer was extracted
  14. dry with materialThe resultant was dried with anhydrous sodium sulfate
  15. distillationthe solvent was distilled off
  16. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-7465963b26004d5689db102ee9fbf938
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…