Dabco → Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

Participants

Reaction Steps

A solution of t-butyl 1-piperazine carboxylate 38 (1.0 g., 5.4 mmole), 5-chloro-2-nitroaniline 54 (0.93 g., 5.4 mmole) and 1,4-diazabicyclo[2.2.2]octane (0.61 g., 54 mmole) in DMSO (10 mL.) was heated 16 hours under argon, cooled to r.t. and diluted with water (150 mL.) and extracted with ethyl acetate (3×50 mL.). The combined organic layers were washed with water (3×30 mL.) and dried over Na2SO4. Solvent was removed and the residue chromatographed (40% EtOAc/Hexane, silica) to give the title compound as a yellow solid, (0.5 g., 30%). MS (M+H)+ 323.

Provenance & Evidence