Ethylamine → 8-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-3,6-dihydroimidazo[4,5-e]indole

HRID 1179430Notes

Reaction equation

HRID 1179430 reaction equation
[CH2:1]([NH2:3])[CH3:2].[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH:6]([C:12]1[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[NH:14][CH:13]=1)[CH2:5]2>CN(C)C=O.O=[Mn]=O>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]1)[CH:6]([C:12]1[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[NH:21][C:1]([CH3:2])=[N:3][C:19]4=3)[NH:14][CH:13]=1)[CH2:5]2

Participants

5

Reactant 2

HCID 6341EthylamineHCID 98162073-(1-azabicyclo[2.2.2]oct-3-yl)-1H-indol-5-ylamine

Product 1

HCID 114488658-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-3,6-dihydroimidazo[4,5-e]indole

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6228DimethylformamideSolvent

Procedure

2 mmol of ethylamine and 10 mmol of MnO2 are added to a solution of 1 mmol of 3-(1-azabicyclo[2.2.2]oct-3-yl)-1H-indol-5-ylamine in 20 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 12 hours. The suspension is filtered through Celite and washed with DMF. After the solvent has been distilled, the mixture is subjected to conventional work-up, giving 8-(1-azabicyclo[2.2.2]oct-3-yl)-2-methyl-3,6-dihydroimidazo[4,5-e]indole; ESI 281.

Workup

  1. filtrationThe suspension is filtered through Celite
  2. washwashed with DMF
  3. distillationAfter the solvent has been distilled

Sources & evidence

ORD record
ord-391542ffb6cf467dadec0eb768da4dd3
Source dataset
uspto-grants-2007_10
Patent number
US07279496B2

Reaction notes

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