Reaktion #155833

Reaktionsgleichung

sodium hydroxide

compound 45

N,N-bis(1H-imidazol-2-ylmethyl)-2-(4-piperidinyl)acetamide trihydrochloride

4-(dipropylamino)butanal

sodium triacetoxyborohydride

→

title compound

2-{1-[4-(dipropylamino)butyl]-4-piperidinyl}-N,N-bis(1H-imidazol-2-ylmethyl)acetamide

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted three times with ethyl acetate
2. 2
   SonstigeThe organic layer was collected
3. 3
   Waschenwashed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

The compound 45 and 4-(dipropylamino)butanal (55.6 mg) were added and a 10% acetic acid-anhydrous dimethyl formamide solution (3 mL) was stirred under an argon atmosphere for 5 minutes. To the reaction solution, sodium triacetoxyborohydride (103 mg) was added, followed by stirring at room temperature for 15 hours. To the reaction solution, an aqueous 2N sodium hydroxide solution (10 mL) was added and the aqueous layer was extracted three times with ethyl acetate. The organic layer was collected, washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain the title compound (86.4 mg) having the following physical properties.

Quelle