Water → (1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

HRID 323487Notes

Reaction equation

HRID 323487 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:16][CH:17]2[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]2)=[CH:2]1.[OH-].[K+].O>C(O)(C)C.O>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[CH:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13587984HCID 13587984, compound

Product 1

HCID 22009357(1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3776IsopropanolSolvent

Procedure

Combine (1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (0.98 g, 2.67 mmol), potassium hydroxide (1.8 g, 32 mmol) in isopropanol (18 mL) containing 1 drop of water. Heat to reflux. After 18 hours, cool, add water, and extract four times with dichloromethane (200 mL). Combine the organic layers, dry over MgSO4, filter, and concentrate in vacuo to give the title compound: Rf=0.40 (silica gel, ethyl acetate).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. extractionextract four times with dichloromethane (200 mL)
  4. dry with materialCombine the organic layers, dry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-65209075db374a14b77e38337c42baa8
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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