3-(5-nitro-1H-indol-3-yl)-1-azabicyclo[2.2.2]oct-2-ene → 3-(1-azabicyclo[2.2.2]oct-3-yl)-1H-indol-5-ylamine

HRID 1179429Notes

Reaction equation

HRID 1179429 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH:14]=1)([O-])=O.[H][H]>CO.[Pd]>[N:15]12[CH2:16][CH2:17][CH:18]([CH2:19][CH2:20]1)[CH:13]([C:7]1[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=3)[NH:9][CH:8]=1)[CH2:14]2

Participants

5

Reactant 2

HCID 574744633-(5-nitro-1H-indol-3-yl)-1-azabicyclo[2.2.2]oct-2-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 98162073-(1-azabicyclo[2.2.2]oct-3-yl)-1H-indol-5-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.2 g of Pd/C (10%) is added to a suspension of 7.4 mmol of 3-(5-nitro-1H-indol-3-yl)-1-azabicyclo[2.2.2]oct-2-ene in 50 ml of methanol, and the mixture is stirred at room temperature for 12 hours in a hydrogen atmosphere at atmospheric pressure. The mixture is filtered, and the filter residue is subjected to conventional work-up, giving 3-(1-azabicyclo[2.2.2]-oct-3-yl)-1H-indol-5-ylamine.

Workup

  1. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-e4b52e1812c349a1ae31330520825ce1
Source dataset
uspto-grants-2007_10
Patent number
US07279496B2

Reaction notes

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