Hydrogen Bromide → HCID 18464428, compound

HRID 1584457Notes

Reaction equation

HRID 1584457 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+]>O>[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

5

Reactant 3

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

Product 1

HCID 18464428HCID 18464428, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (5.95 g, 20.6 mmol) and 48% hydrobromic acid (50 mL). Heat to reflux. After 3.5 hours, cool the reaction mixture and dilute with a solution of sodium hydroxide (23 g, 0.57 mmol) in water (250 mL). Extract three times with dichloromethane. Combine the aqueous layer, dichloromethane (200 mL), and sodium chloride (50 g) and stir. After 18 hours, separate the layers and combine all the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give 4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool the reaction mixture
  3. extractionExtract three times with dichloromethane
  4. waitAfter 18 hours
  5. customseparate the layers
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-ec1edf472bd84f3aaf241492e8a23389
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

Loading…