Reaction #319849

Reaction equation

2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-chloro-5-nitrotoluene

potassium fluoride

cyclopropylamine

→

3-(4-methyl-1-piperazinyl)-4-fluoro-5-chloro-2-methyl-6-nitro-N-cyclopropylaniline

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionextracted with dichloromethane
3. 3
   Otherthe extract is dried
4. 4
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
5. 5
   Otherpurified by silica-gel column-chromatography (eluent; dichloromethane: methanol=10:1)

Procedure

To the thus obtained 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-chloro-5-nitrotoluene (0.13 g) are added anhydrous dimethylformamide (2 ml), potassium fluoride (37 mg) and cyclopropylamine (0.15 ml) and the mixture is stirred at 100° C. for 3 hours. After cooling, the reaction mixture is poured into ice-water, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and purified by silica-gel column-chromatography (eluent; dichloromethane: methanol=10:1) to give 3-(4-methyl-1-piperazinyl)-4-fluoro-5-chloro-2-methyl-6-nitro-N-cyclopropylaniline (0.14 g).

Source