Hydrogen Bromide → HCID 18464457, compound

HRID 2230555Notes

Reaction equation

HRID 2230555 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+].[ClH:25]>O.O1CCOCC1.CO>[ClH:25].[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

8

Reactant 4

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

Product 1

HCID 18464457HCID 18464457, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (5.10 g, 1.8 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. Triturate the residue with diethyl ether to give a solid. Collect the solid by filtration and dry 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. customTriturate the residue with diethyl ether
  10. customto give a solid
  11. customCollect the solid
  12. filtrationby filtration
  13. customdry

Sources & evidence

ORD record
ord-561a21689ce747508883b078b4f179e9
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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