Sodium Iodide → HCID 10645969, compound

HRID 249246Notes

Reaction equation

HRID 249246 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:15][N:16]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:2].Cl[CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH:32]=[CH:31][CH:30]=[CH:29]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:15][N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][CH:30]=[CH:29]2)[CH2:18][CH2:17]1)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 13656992HCID 13656992, compoundHCID 19760868HCID 19760868, compound

Product 1

HCID 10645969HCID 10645969, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2.42 g (8 mmol) of 1-(2-ethoxyethyl)-2-(homopiperazin-1-yl-methyl)benzimidazole, 1.39 g (8.8 mmol) of 1-(4-chlorobutyl)pyrrole, 1.65 g (12 mmol) of potassium carbonate and 1.65 g (11 mmol) of sodium iodide in 40 ml of methyl ethyl ketone is refluxed for 16 hours. The mixture is cooled, filtered and the filtrate evaporated to dryness. The residue is taken up in chloroform and washed with water, dried, filtered and evaporated under vacuum. The resulting product is purified on a silica chromatographic column (eluent: chloroform-methanol 92:8) and 1.9 g (56%) of 1-(2-ethoxyethyl)-2-{4-[4-(pyrrol-1-yl)butyl]homopiperazin-1-yl-methyl}benzimidazole are obtained.

Workup

  1. temperatureis refluxed for 16 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customThe resulting product is purified on a silica chromatographic column (eluent: chloroform-methanol 92:8) and 1.9 g (56%) of 1-(2-ethoxyethyl)-2-{4-[4-(pyrrol-1-yl)butyl]homopiperazin-1-yl-methyl}benzimidazole
  10. customare obtained

Sources & evidence

ORD record
ord-357c2b1f6e684e4d96209756a6da630d
Source dataset
uspto-grants-1993_05
Patent number
US05214040

Reaction notes

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