1H-imidazole-2-carbaldehyde → (4-dipropylaminomethylphenyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-amine

HRID 348639Notes

Reaction equation

HRID 348639 reaction equation
[NH2:1][CH2:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O>CO>[CH2:17]([N:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:30][C:26]3[NH:25][CH:29]=[CH:28][N:27]=3)=[CH:24][CH:23]=2)=[CH:10][CH:11]=1)[CH2:20][CH2:21][CH3:22])[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 249551H-imidazole-2-carbaldehydeHCID 23079293(4-Aminomethylbenzyl)-(4-dipropylaminomethylphenyl)-amine

Product 1

HCID 21084473(4-dipropylaminomethylphenyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-amineYield 59.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (63.1 mg) obtained in Example 39-2 was dissolved in methanol (2.0 ml) and then added with 2-imidazole carboxaldehyde (17.9 mg), followed by stirring at room temperature for 17 hours. After the solvent had been distilled off, the residue was dried under vacuum and then dissolved in methanol (2.5 ml). Subsequently, the solution was added with sodium borohydride (14.5 mg) and stirred at room temperature for 1 hour. The reaction solution was added with a saturated aqueous ammonium chloride solution (4.0 ml) and stirred at room temperature for 30 minutes. Then, the reaction solution was added with saturated saline solution and subjected to extraction with chloroform, followed by drying with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/acetone), thereby obtaining the subject compound (45.2 mg) as a yellow solid.

Workup

  1. distillationAfter the solvent had been distilled off
  2. customthe residue was dried under vacuum
  3. dissolutiondissolved in methanol (2.5 ml)
  4. additionSubsequently, the solution was added with sodium borohydride (14.5 mg)
  5. stirringstirred at room temperature for 1 hour
  6. additionThe reaction solution was added with a saturated aqueous ammonium chloride solution (4.0 ml)
  7. stirringstirred at room temperature for 30 minutes
  8. additionThen, the reaction solution was added with saturated saline solution
  9. extractionsubjected to extraction with chloroform
  10. dry with materialby drying with anhydrous sodium sulfate
  11. distillationAfter the solvent had been distilled off
  12. customthe residue obtained
  13. customwas purified through silica gel column chromatography (chloroform/acetone)

Sources & evidence

ORD record
ord-b399dc5440414eb396ab69c3600b19af
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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