Ethanol → 4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

HRID 1584483Notes

Reaction equation

HRID 1584483 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)C.[IH:35]>C(OCC)C>[IH:35].[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:19]2[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:16]=[C:15]2[N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24841Hydrogen iodideHCID 184648461-t-butoxycarbonyl-4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 865839014-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-t-butoxycarbonyl-4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)[1,4]diazepane (1.12 g, 2.64 mmol) and ethanol (15 mL). Add aqueous hydriodic acid (5 mL, 57%). Heat to reflux. After 1 hour, cool to ambient temperature and dilute with diethyl ether (250 mL) and stir to give a solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give the title compound: Rf =0.16 (silica gel, 10% methanol/dichloromethane/0.01% concentrated aqueous ammonia.

Workup

  1. temperatureHeat to reflux
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with diethyl ether
  6. customdry

Sources & evidence

ORD record
ord-f03a8ccb11884589a557f041a8414805
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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