Water → 1-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine

HRID 323479Notes

Reaction equation

HRID 323479 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[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(OCC)=O)[CH2:19][CH2:18]1.[OH-].[K+].O.NN.O>C(O)CO.ClCCl.CO.CO.C(OCC)(=O)C.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[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

Participants

10

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 13587981(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Product 1

HCID 135879951-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 5

HCID 174Ethylene GlycolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent3×

Procedure

Combine (1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (1.38 g, 3.75 mmol), potassium hydroxide (3.0 g, 56.1 mmol) in ethylene glycol (15 mL). Add hydrazine hydrate (3.09 mL, 63.7 mmol). 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 obtain a residue. Chromatograph the residue on silica gel eluting with sequentially with ethyl acetate, 25% methanol/ethyl acetate, 50% methanol/ethyl acetate, 75% methanol/ethyl acetate, and then methanol to give a residue. Dissolve the residue in dichloromethane, extract with water and then brine, dry over MgSO4, filter, and evaporate in vacuo to give the title compound.

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
  7. customto obtain a residue
  8. extractionextract with water
  9. dry with materialbrine, dry over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo

Sources & evidence

ORD record
ord-9141a55894aa4b809a238c8def6b840c
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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