Reaction #155350

Reaction equation

N-methylpiperazine

sodium iodide

potassium carbonate

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline 2-carboxy-(2-chloroethyl)amide

→

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline 2-carboxy-[2-(4-methylpiperazin-1-yl)ethyl]amide

Yield 14.1%

Solvents

DMF

water

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to room temperature
2. 2
   Extractionfollowed by extraction
3. 3
   ConcentrationThe thus-obtained organic layer was concentrated under reduced pressure
4. 4
   Otherthe residue was then purified
5. 5
   ConcentrationThe purified product was concentrated under reduced pressure

Procedure

N-methylpiperazine (276 mg, 2.76 mmol), sodium iodide (440 mg, 2.9 mmol) and potassium carbonate (572 mg, 4.14 mmol) were added to a DMF solution (8 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxy-(2-chloroethyl)amide (600 mg, 1.38 mmol) and stirred overnight at 80° C. The mixture was cooled to room temperature, and water was then added thereto, followed by extraction using chloroform. The thus-obtained organic layer was concentrated under reduced pressure, and the residue was then purified using medium pressure liquid chromatography (NH silica gel, dichloromethane:methanol=100:0→10:1). The purified product was concentrated under reduced pressure, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline-2-carboxy-[2-(4-methylpiperazin-1-yl)ethyl]amide (100 mg, yield: 14%).

Source