HCID 178526667, compound → 3-[1-(4-aminophenyl)pyrrolidin-3-yl]-1-(3-{1-[1-(4-aminophenyl)pyrrolidin-3-yl]-1H-imidazol-3-ium-3-yl}propyl)-1H-imidazol-3-ium dibromide

HRID 583723Notes

Reaction equation

HRID 583723 reaction equation
[Br-:1].[Br-].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][CH:14]([N+:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][CH2:24][N+:25]4[CH:29]=[CH:28][N:27]([CH:30]5[CH2:34][CH2:33][N:32]([C:35]6[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=6)[CH2:31]5)[CH:26]=4)[CH:18]=3)[CH2:13]2)=[CH:8][CH:7]=1)([O-])=O>O.C(O)C.[Pd]>[Br-:1].[Br-:1].[NH2:3][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][CH:14]([N+:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][CH2:24][N+:25]4[CH:29]=[CH:28][N:27]([CH:30]5[CH2:34][CH2:33][N:32]([C:35]6[CH:36]=[CH:37][C:38]([NH2:41])=[CH:39][CH:40]=6)[CH2:31]5)[CH:26]=4)[CH:18]=3)[CH2:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 178526667HCID 178526667, compound

Product 1

HCID 1785076973-[1-(4-aminophenyl)pyrrolidin-3-yl]-1-(3-{1-[1-(4-aminophenyl)pyrrolidin-3-yl]-1H-imidazol-3-ium-3-yl}propyl)-1H-imidazol-3-ium dibromide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3.2 g (0.0044 mol) of derivative (4) above dissolved in a mixture of 60 ml of water/300 ml of ethanol were hydrogenated in the presence of palladium-on-charcoal under a hydrogen pressure of 9 bar and at 75° C. After filtering off the catalyst, the expected derivative (5) was isolated in the form of the hydrobromide. 3.4 g of white powder were obtained; 94% yield.

Workup

  1. customat 75° C
  2. filtrationAfter filtering off the catalyst

Sources & evidence

ORD record
ord-af8631f9267e4fd6ac04d17a5cf0f287
Source dataset
uspto-grants-2005_08
Patent number
US06923835B2

Reaction notes

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