Diethyl Ether → (1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

HRID 323504Notes

Reaction equation

HRID 323504 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1)([O:3][CH2:4][CH3:5])=[O:2].[IH:32].C(OCC)C>C(O)C>[IH:32].[C:1]([CH2:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24841Hydrogen iodideHCID 22009256(1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Product 1

HCID 86756600(1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine (1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (0.59 g, 1.37 mmol) and aqueous hydriodic acid (2 mL, 57%) in ethanol (25 mL). Heat to reflux. After 2 hours, cool to ambient temperature, pour the reaction mixture into diethyl ether (450 mL), and cool to about −30° C. to give a solid. Collect the solid by filtration and dry to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool to about −30° C.
  3. customto give a solid
  4. customCollect the solid
  5. filtrationby filtration
  6. customdry

Sources & evidence

ORD record
ord-c88fde4ce1794f76aee8f5049c1d2690
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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