Reaction #86479

Reaction equation

tert-butyl 4-(4-(1,3-dioxoisoindolin-2-yl)-3-nitrophenyl)piperazine-1-carboxylate

Hydrazine

EtOAc water

→

title compound

Yield 94.1%

tert-butyl 4-(4-amino-3-nitrophenyl)piperazine-1-carboxylate

Yield 94.1%

Solvents

THF

THF

Conditions

Workup

1. 1
   Washwas washed with brine
2. 2
   Dryingdried over MgSO4
3. 3
   Otherevaporated
4. 4
   OtherThe resulting oil was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane

Procedure

To a suspension of tert-butyl 4-(4-(1,3-dioxoisoindolin-2-yl)-3-nitrophenyl)piperazine-1-carboxylate (275.4 g, 0.6 mmol) in THF (5.0 ml) was added 1.0M Hydrazine in THF (1.8 ml, 1.8 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into EtOAc/water and organic layer was washed with brine, dried over MgSO4 and evaporated. The resulting oil was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane to afford the title compound (182 mg, 93% yield). 1H-NMR (400 MHz, DMSO-d6) δ 1.42 (s, 9H) 2.89-2.99 (m, 4H) 3.44 (d, 4H) 6.98 (d, 1H) 7.22 (s, 2H) 7.26-7.38 (m, 2H)

Source