Ethanol → HCID 86754358, compound

HRID 1584481Notes

Reaction equation

HRID 1584481 reaction equation
CO.ClCCl.C(OC([N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]2[N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:23]3[CH:30]=[CH:31][CH:32]=[CH:33][C:22]=3[N:21]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.C(O)C.[IH:37]>C(OCC)C>[IH:37].[CH2:25]([N:24]1[C:23]2[CH:30]=[CH:31][CH:32]=[CH:33][C:22]=2[N:21]=[C:20]1[N:16]1[CH2:17][CH2:18][CH2:19][NH:13][CH2:14][CH2:15]1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 24841Hydrogen iodideHCID 212238131-t-butoxycarbonyl-4-(1-pentyl-1H-benzimidazol-2-yl)[1,4]diazepaneHCID 21226129Dichloromethane methanol

Product 1

HCID 86754358HCID 86754358, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (0.8 g, 2.5 mmol) in dimethylformamide (10 mL). Add sodium hydride (0.13 g, 60% in oil, 3.25 mmol) portionwise. After about 30 minutes, when the gas evolution ceases, add pentyl bromide (0.34 mL, 2.74 mmol). Heat to 80° C. After 18 hours, cool the reaction mixture and dilute with dichloromethane (150 mL) and extract with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 1-t-butoxycarbonyl-4-(1-pentyl-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.87 (silica gel, 5% methanol/dichloromethane/0.05% concentrated aqueous ammonia). Combine 1-t-butoxycarbonyl-4-(1-pentyl-1H-benzimidazol-2-yl)[1,4]diazepane (0.7 g, 1.8 mmol) and ethanol (5 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.

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-6ed38e37ed1e4618a98943964f4cd0a9
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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