Dichloromethane → 4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

HRID 1584477Notes

Reaction equation

HRID 1584477 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.ClCCl.[IH:27]>CO>[IH:27].[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24841Hydrogen iodideHCID 698341014-(fur-2-ylmethyl-1H-benzimidazol-2-yl)[1,4]diazepane hydrochloric acid salt

Product 1

HCID 867543564-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydrochloric acid salt (0.57 g, 1.53 mmol) and dichloromethane (150 mL). Extract with a saturated aqueous solution of sodium bicarbonate, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Combine the residue and methanol (50 mL). Cool in an ice bath. Add aqueous hydriodic acid (0.194 g, 57%, 1.52 mmol). After 30 minutes, evaporate to remove most of the methanol and triturate with diethyl ether (150 mL) to give a solid. Decant the solvent, add diethyl ether (150 mL) and collect the solid by filtration to give, after drying, the title compound.

Workup

  1. extractionExtract with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue
  6. temperatureCool in an ice bath
  7. customevaporate
  8. customto remove most of the methanol
  9. customtriturate with diethyl ether (150 mL)
  10. customto give a solid
  11. customDecant the solvent
  12. additionadd diethyl ether (150 mL)
  13. customcollect the solid
  14. filtrationby filtration
  15. customto give
  16. customafter drying

Sources & evidence

ORD record
ord-aee7400fdee042e8ab3e7ad89e4084cf
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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