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

HRID 2230688Notes

Reaction equation

HRID 2230688 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[N:16]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:4][CH:3]=1.[IH:25].C(O)C>C(OCC)C>[IH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[N:16]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24841Hydrogen iodideHCID 184649032-[1,4]Diazepan-1-YL-1-(4-fluoro-benzyl)-1H-benzoimidazole

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 (2.50 g, 5.89 mmol), aqueous hydriodic acid (5 mL, 57%), and ethanol (10 mL). Heat to reflux. After 1 hour, cool to ambient temperature and pour the reaction mixture into diethyl ether (450 mL) and stir to give a solid. After 1 hour, collect the solid by filtration, rinse with diethyl ether, and dry in vacuo to give the title compound: Rf=0.16 (silica gel, dichloromethane/methanol/concentrated aqueous ammonia 90/10/0.1).

Workup

  1. temperatureHeat to reflux
  2. customto give a solid
  3. waitAfter 1 hour
  4. customcollect the solid
  5. filtrationby filtration
  6. washrinse with diethyl ether
  7. customdry in vacuo

Sources & evidence

ORD record
ord-ed197ef625834f9f8ec89b28479dfa99
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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