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

HRID 58201Notes

Reaction equation

HRID 58201 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)=[CH:14][C:13]=1[N+:31]([O-:33])=[O:32].NN.CCOC(C)=O.O>C1COCC1>[NH2:3][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[N+:31]([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 22728543Water ethylacetateHCID 118025495Tert-butyl 4-(4-(1,3-dioxoisoindolin-2-yl)-3-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 117722366Tert-butyl 4-(4-amino-3-nitrophenyl)piperazine-1-carboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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)

Workup

  1. washwas washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe resulting oil was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane

Sources & evidence

ORD record
ord-53b1806e9a9249e69f58b793ec7524a2
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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