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

HRID 1179428Notes

Reaction equation

HRID 1179428 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[OH-].[K+].[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2)([O-:15])=[O:14]>O.CO>[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:4]1[CH:5]2[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]2)[CH:3]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 225235-NitroindoleHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 574744633-(5-nitro-1H-indol-3-yl)-1-azabicyclo[2.2.2]oct-2-ene

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

44.8 mmol of 1-azabicyclo[2.2.2]octan-3-one hydrochloride (3-quinuclidinone hydrochloride) and 112 mmol of potassium hydroxide are added to a solution of 22.4 mmol of 5-nitro-1H-indole in 100 ml of water/methanol (1/1), and the mixture is stirred at the boiling point for 48 hours. The crystals which deposit on cooling of the reaction solution are filtered off, washed and dried, giving 3-(5-nitro-1H-indol-3-yl)-1-azabicyclo[2.2.2]-oct-2-ene.

Workup

  1. temperatureThe crystals which deposit on cooling of the reaction solution
  2. filtrationare filtered off
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-513ca5a922ae48aba26dcd556aa83060
Source dataset
uspto-grants-2007_10
Patent number
US07279496B2

Reaction notes

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