Hydrogen Bromide → HCID 18464428, compound

HRID 637081Notes

Reaction equation

HRID 637081 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-01bd628a01714b5c98bc99fa70c5608d
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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