Reaction #319833

Reaction equation

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

potassium fluoride

cyclopropylamine

→

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

Solvents

dimethyl sulfoxide

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
   Otherthe residue is purified by silica-gel column-chromatography (dichloromethane: methanol=40:1)

Procedure

To 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-methyl-5-nitrotoluene (1.73 g) are added anhydrous dimethyl sulfoxide (18 ml), potassium fluoride (0.53 g) and cyclopropylamine (2.2 ml) and the mixture is stirred at 100° C. for 23 hours. After cooling, the mixture is poured into ice-water, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane: methanol=40:1) to give 3-(4-methyl-1-piperazinyl)-4-fluoro-2,5-dimethyl-6-nitro-N-cyclopropylaniline (1.65 g).

Source