Indole → 5-[(Indol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole

HRID 1440039Notes

Reaction equation

HRID 1440039 reaction equation
Cl.[N:2]1[C:6]2[CH2:7][CH2:8][CH:9]([C:11](N3CCCC3)=[O:12])[CH2:10][C:5]=2[NH:4][CH:3]=1.ClC(Cl)C.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.P(Cl)(Cl)(Cl)=O>C(=O)([O-])[O-].[K+].[K+]>[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:11]([CH:9]2[CH2:8][CH2:7][C:6]3[N:2]=[CH:3][NH:4][C:5]=3[CH2:10]2)=[O:12])=[CH:23]1

Participants

6

Reactant 4

HCID 798IndoleHCID 63651,1-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 18985210Pyrrolidin-1-yl(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-5-yl)methanone hydrochloride

Product 1

HCID 107541665-[(Indol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazoleYield 43.9%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

4 g of N-[(4,5,6,7-tetrahydrobenzimidazol-5-yl)carbonyl]pyrrolidine hydrochloride obtained in Example 5 were added to 40 ml of dichloroethane, and 2.74 g of indole and 4.4 ml of phosphorus oxychloride were added thereto. The mixture was stirred at 80° to 85° C. for 7 hours and then at room temperature overnight. To the mixture was added 40 ml of a cold potassium carbonate aqueous solution, followed by extraction with chloroform. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography using chloroform/methanol as an eluent to obtain 1.82 g of 5-[(indol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole as a foam-like substance. In 1 ml of methanol were dissolved 0.16 g of the resulting product and 0.06 g of fumaric acid, and 5 ml of acetonitrile was added to the solution. The formed crystal was collected by filtration to obtain 0.13 g of 5-[(indol- 3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole fumarate.

Workup

  1. additionwere added
  2. customat room temperature
  3. customovernight
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c15376c5953649a2a105978e37eb1fb8
Source dataset
uspto-grants-1996_03
Patent number
US05496942

Reaction notes

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