Ethylenediamine → HCID 178420740, compound

HRID 1179431Notes

Reaction equation

HRID 1179431 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[CH:7]([C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[C:19](O)[CH:20]=3)[NH:15][CH:14]=1)[CH2:6]2.OC1C=C2C(=CC=1)NC=C2.N12CCC(CC1)C(=O)C2>CN(C=O)C.O=[Mn]=O>[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[CH:7]([C:13]1[C:21]3[C:20]4[N:3]=[CH:2][CH:1]=[N:4][C:19]=4[CH:18]=[CH:17][C:16]=3[NH:15][CH:14]=1)[CH2:6]2

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 160545-HydroxyindoleHCID 195073-QuinuclidinoneHCID 98346891H-Indol-5-ol, 3-(1-azabicyclo[2.2.2]oct-3-yl)-

Product 1

HCID 178420740HCID 178420740, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6228DimethylformamideSolvent

Procedure

0.2 mmol of ethane-1,2-diamine and 1 mmol of MnO2 are added to a solution of 0.1 mmol of 3-(1-azabicyclo[2.2.2]oct-3-yl)-1H-indol-5-ol (prepared analogously to Example 1.1 to 1.2 by reaction of 5-hydroxy-1H-indole with 3-quinuclidinone followed by hydrogenation) in 2 ml of DMF, and the mixture is stirred at room temperature for 18 hours. The suspension is filtered through Celite and subjected to conventional work-up, giving 9-(1-azabicyclo[2.2.2]oct-3-yl)-7H-pyrrolo[3,2-f]quinoxaline; ESI 279.

Workup

  1. filtrationThe suspension is filtered through Celite

Sources & evidence

ORD record
ord-2405239724a34a10a8b3e2c82cc2ea10
Source dataset
uspto-grants-2007_10
Patent number
US07279496B2

Reaction notes

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