Hydrazine → 7-[3-(Trifluoromethyl)piperazin-1-yl]-1-benzofuran-5-amine

HRID 1162019Notes

Reaction equation

HRID 1162019 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH:15]([C:19]([F:22])([F:21])[F:20])[CH2:14]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.NN>C1COCC1.CCO.[Ni]>[F:21][C:19]([F:20])([F:22])[CH:15]1[NH:16][CH2:17][CH2:18][N:13]([C:6]2[C:7]3[O:11][CH:10]=[CH:9][C:8]=3[CH:12]=[C:4]([NH2:1])[CH:5]=2)[CH2:14]1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 668920161-(5-Nitro-1-benzofuran-7-yl)-3-(trifluoromethyl)piperazine2×

Product 1

HCID 668933657-[3-(Trifluoromethyl)piperazin-1-yl]-1-benzofuran-5-amineYield 63%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(5-Nitro-1-benzofuran-7-yl)-3-(trifluoromethyl)piperazine (96.6 mg, 0.31 mmol; Intermediate 46) was dissolved in THF (6 mL) and EtOH (25 mL). Raney nickel (slurry in ethanol; 1 mL) and H2NNH2 (61.4 mg, 1.23 mmol) were added and the mixture was stirred at room temperature overnight. Filtration through Celite and concentration gave 7-[3-(trifluoromethyl)piperazin-1-yl]-1-benzofuran-5-amine (55 mg, 63%). This material was used in the next reaction step without further purification.

Workup

  1. filtrationFiltration
  2. concentrationthrough Celite and concentration

Sources & evidence

ORD record
ord-5e7ecdad6b55464297c350a36bb1f5b5
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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