Reaction #155351

Reaction equation

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

Yield 35.4%

Solvents

Dichloromethane

Conditions

Workup

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

Procedure

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