Tetrahydrofuran → 7-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-amine

HRID 1161999Notes

Reaction equation

HRID 1161999 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:13][CH:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.C1COCC1.NN>C(O)C.[Ni]>[N:16]12[CH2:21][CH2:20][CH:19]([CH2:18][CH2:17]1)[CH:14]([O:13][C:6]1[C:7]3[O:11][CH:10]=[CH:9][C:8]=3[CH:12]=[C:4]([NH2:1])[CH:5]=1)[CH2:15]2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 66893251HCID 66893251, compound

Product 1

HCID 668930057-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-amineYield 40.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

3-[(5-Nitro-1-benzofuran-7-yl)oxy]quinuclidine (1.38 g, 4.79 mmol; obtained in Step 1) was dissolved in ethanol:THF (100 mL: 25 mL) and Raney-nickel (slurry in ethanol; 6 mL) and hydrazine (891 μL, 0.18 mmol) were added. The mixture was stirred at room temperature for 3 h and then filtered through Celite and the solvent was removed in vacuo. The crude product was purified by flash chromatography [eluent: DCM:methanol (6:1) and chloroform:MeOH:triethylamine (9:1:0.1)] to give 7-(1-azabicyclo[2.2.2]oct-3-yloxy)-1-benzofuran-5-amine (500 mg; 40%).

Workup

  1. filtrationfiltered through Celite
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography [eluent: DCM:methanol (6:1) and chloroform:MeOH:triethylamine (9:1:0.1)]

Sources & evidence

ORD record
ord-c8e156baf1fc4c3f8b04b6029dab228e
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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