p-Fluoronitrobenzene → HCID 58976363, compound

Participants

Reaction Conditions

Reaction Steps

1-Cyclopropylpiperazine (268, 1.76 g, 14.0 mmol) was dissolved in 15 mL DMF. To it were added 1-fluoro-4-nitrobenzene (1.00 g, 7.0 mmol) and DIEA (1.24 mL, 7.0 mmol). The mixture was stirred at 90° C. for overnight, cooled to RT, diluted with EtOAc, washed with water ×2, dried, concentrated in vacuo, subjected to silica flash column using 0 to 40% EtOAc in DCM to isolate 1-cyclopropyl-4-(4-nitrophenyl)piperazine (269). It was dissolved in 2:1 EtOAc/MeOH (80 mL/40 mL), and to it were added 40 μL 6N HCl and 10% Pd/C (0.5 g). The mixture was stirred at RT for overnight under a hydrogen balloon. It was filtered through celite, concentrated in vacuo to dryness to afford 4-(4-cyclopropylpiperazin-1-yl)aniline hydrochloride (270, 1.30 g, 73% overall) as an off-white solid.

Provenance & Evidence