Methanol → (1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

HRID 323491Notes

Reaction equation

HRID 323491 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)=[O:5])[CH3:2].[IH:30].CO>C(OCC)C>[IH:30].[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 24841Hydrogen iodideHCID 22009058(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Product 1

HCID 86756599(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine (1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (0.405 g, 1.00 mmol), aqueous hydriodic acid (0.29 mL, 57%), and methanol (15 mL). Heat to reflux. After 2 hour, cool to ambient temperature and add diethyl ether (100 mL) and stir to give a solid. After 1 hour, collect the solid by filtration, dissolve in methanol and add diethyl ether (100 mL) to give a solid. Collect the solid by filtration and dry in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customto give a solid
  3. waitAfter 1 hour
  4. customcollect the solid
  5. filtrationby filtration
  6. dissolutiondissolve in methanol
  7. additionadd diethyl ether (100 mL)
  8. customto give a solid
  9. customCollect the solid
  10. filtrationby filtration
  11. customdry in vacuo

Sources & evidence

ORD record
ord-3e0dfca92e3446babd318c8e3c5096d3
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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