Isopropanol → (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzoimidazole-2-yl)(piperidin-4-yl)amine

HRID 582071Notes

Reaction equation

HRID 582071 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22](C(OCC)=O)[CH2:21][CH2:20]2)=[CH:5][CH:4]=1.[OH-].[K+].C(O)(C)C>O>[OH:1][CH2:2][C:3]1[O:7][C:6]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 22009043(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Product 1

HCID 22009201(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzoimidazole-2-yl)(piperidin-4-yl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine (1 mmol), potassium hydroxide (1.2 mmcl), and isopropanol (20 mL). Heat to reflux. After 18 hours, evaporate intcacuo to give a residue. Combine the resczue and water. Extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customevaporate intcacuo
  3. customto give a residue
  4. extractionExtract with dichloromethane
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-d21f8daaa0be4e20a557898196d14481
Source dataset
uspto-grants-1999_07
Patent number
US05922737

Reaction notes

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