Reacción #86479

Ecuación de reacción

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

Hydrazine

EtOAc water

→

title compound

Rendimiento 94.1%

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

Rendimiento 94.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowas washed with brine
2. 2
   Secadodried over MgSO4
3. 3
   Otroevaporated
4. 4
   OtroThe resulting oil was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane

Procedimiento

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)

Fuente