[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.[Cl-].[NH4+]>C(O)C.[Fe]>[CH3:1][CH:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:3]1To a mixture of (±)-tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate (870 mg) and iron powder (378 mg) in ethanol (16 ml) was added an aqueous solution (4 ml) of ammonium chloride (116 mg) at room temperature. The resulting suspension was refluxed for 2 hours with vigorous stirring. The reaction mixture was cooled to room temperature, and the resulting solid was filtered through celite and thoroughly washed with ethyl acetate. The filtrate was separated, and the aqueous layer was extracted with ethyl acetate twice. The organic layers were combined and washed successively with saturated aqueous sodium hydrogencarbonate solution and brine. The solvent was evaporated to give the title compound as a yellow oil.
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