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

HRID 323479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323479
[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

Komponenten

10

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 174Ethylene GlycolLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9141a55894aa4b809a238c8def6b840c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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