Reaktion #435903

Reaktionsgleichung

sodium borohydride

compound

4-dipropylaminomethyl benzaldehyde

trimethyl orthoformate

compound

N-(1H-imidazol-2-ylmethyl)-N-(1-methyl-1H-imidazol-2-ylmethyl)butane-1,4-diamine

→

N-(4-dipropylaminomethylbenzyl)-N′-(1H-imidazol-2-ylmethyl)-N′-(1-methyl-1H-imidazol-2-ylmethyl)-1,4-butanediamine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby cooling to 0° C
2. 2
   workup.STIRRINGstirred at room temperature for 30 minutes
3. 3
   SonstigeAfter completion of the reaction
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   Waschenwashed with an aqueous sodium bicarbonate solution
7. 7
   Extraktionfollowed by extraction with chloroform
8. 8
   WaschenThe organic layer was washed with saturated saline solution
9. 9
   Trocknendried with anhydrous sodium sulfate
10. 10
    FiltrationAfter filtration
11. 11
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
12. 12
    SonstigeThe residue was purified through silica gel column chromatography (chloroform)
13. 13
    workup.ADDITIONtreated with hydrochloric acid

Vorschrift

The compound (349 mg) obtained in Example 117-4 was dissolved in methanol (7.0 ml). Then, the solution was added with the compound (323 mg) obtained in Example 117-1 and trimethyl orthoformate (0.340 ml) and stirred at room temperature for 2 hours, followed by cooling to 0° C. The solution was added with sodium borohydride (75.5 mg) and stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with an aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform) and treated with hydrochloric acid, thereby obtaining hydrochloride (89.8 mg) of the subject compound as a white solid.

Quelle