Réaction #155351

Équation de réaction

Sodium triacetoxyborohydride

1-(2-Pyridyl)piperazine

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde

→

5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one

Rendement 35.4%

Solvants

Dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred at room temperature for 4 hours
2. 2
   Lavagewashed with water
3. 3
   Séchagethe mixture was dried over sodium sulfate
4. 4
   AutreThereafter, the solvent was removed under reduced pressure
5. 5
   AutreThe residue was then purified
6. 6
   AutreThe solvent was removed under reduced pressure
7. 7
   Autrethe residue was recrystallized from ethyl acetate-n-hexane

Mode opératoire

1-(2-Pyridyl)piperazine (551 mg, 3.38 mmol) was added to a 1,2-dichloromethane solution (20 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde (800 mg, 2.25 mmol) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (670 mg, 3.16 mmol) was added to the resulting mixture and stirred at room temperature for 4 hours. Dichloromethane was added to the resulting reaction mixture, washed with water, and then the mixture was dried over sodium sulfate. Thereafter, the solvent was removed under reduced pressure. The residue was then purified using NH silica gel column chromatography (dichloromethane:ethyl acetate=1:1). The solvent was removed under reduced pressure and the residue was recrystallized from ethyl acetate-n-hexane, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one (400 mg, yield: 35%).

Source