Hydrazine hydrate (1:1) → HCID 21864857, compound

HRID 1161982Notes

Reaction equation

HRID 1161982 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.O.NN>C1COCC1.CCO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21864772HCID 21864772, compound

Product 1

HCID 21864857HCID 21864857, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

tert-Butyl 4-(5-nitro-1-benzofuran-7-yl)piperazine-1-carboxylate* (1 g, 2.9 mmol) was dissolved in THF/EtOH (1:4). An excess of Raney-Ni (slurry in ethanol) was added followed by hydrazine-hydrate (0.58 g, 11.5 mmol). The reaction mixture was stirred at room temperature overnight. Filtration and evaporation afforded 1.19 g of the title product that was used in the next step without further purification. HPLC purity 93%, RT=1.71 min (System A; 10-97% MeCN over 3 min). *Previously described in WO 2002100822.

Workup

  1. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-48d4b0fd84d5455e8c1d664ca2ee849a
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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