Reaction #1725850

Reaction equation

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

potassium fluoride

cyclopropylamine

→

N-cyclopropyl-2-methyl-3-(4-ethoxycarbonyl-1-piperazinyl)-4-fluoro-6-nitroaniline

Yield 93.7%

Solvents

dimethylsulfoxide

Conditions

Workup

1. 1
   Extractionextracted with dichloromethane
2. 2
   workup.DISTILLATIONThe solvent is distilled off
3. 3
   Otherthe residue is recrystallized from ethanol

Procedure

To 3,6-difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrotoluene (7.1 g) are added anhydrous dimethylsulfoxide (23 ml), potassium fluoride (2.0 g) and cyclopropylamine (1.5 g), and the mixture is heated at 60° C. for 6 hours. The reaction mixture is poured into ice water, and extracted with dichloromethane. The solvent is distilled off and the residue is recrystallized from ethanol to give N-cyclopropyl-2-methyl-3-(4-ethoxycarbonyl-1-piperazinyl)-4-fluoro-6-nitroaniline (7.4 g), as orange red prisms, m.p. 97°-98° C.

Source