Hydrogen Bromide → HCID 18464428, compound

HRID 1584446Notes

Reaction equation

HRID 1584446 reaction equation
C([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[N:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)C.Br.[OH-].[Na+].Cl>O.O1CCOCC1.ClCCl.CO>[OH: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[N:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

9

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9984168Emedastine EP Impurity E

Product 1

HCID 18464428HCID 18464428, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (5.10 g, 9.4 mmol) and 48% hydrobromic acid (25 mL). Heat to reflux. After 18 hours, dilute with water and adjust the pH to 12 using aqueous 5 M sodium hydroxide solution. Extract three times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Combine the residue and methanol (50 mL). Add a solution of hydrochloric acid (5.0 mL, 4 M, 20 mmol) in dioxane. Evaporate in vacuo to give a residue. Combine the give residue and dichloromethane. Extract with a saturated aqueous solution of sodium bicarbonate. Dry the organic layers over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. extractionExtract three times with dichloromethane
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. customEvaporate in vacuo
  8. customto give a residue
  9. extractionExtract with a saturated aqueous solution of sodium bicarbonate
  10. dry with materialDry the organic layers over Na2SO4
  11. filtrationfilter
  12. customevaporate in vacuo

Sources & evidence

ORD record
ord-a17d8b7e40954e4e8f5f5cd089267049
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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