Ethanol → 5-Acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole

HRID 1633601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633601
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][CH:16]=3)[CH:10]=2)=[C:6]([N+:24]([O-])=O)[CH:5]=1)(=[O:3])[CH3:2].[CH2:27](O)C>[Pd]>[C:1]([C:4]1[CH:23]=[CH:22][C:7]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]4[CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH2:20]4)[CH:10]=3)[CH:27]=[N:24][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 227418634-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline

Produkt 1

HCID 227418345-Acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline (6, Ex. 12a) (1 g, 3 mmol) in ethanol (50 ml) was added a catalytic amount of palladium on charcoal and the mixture was hydrogenated at ambient pressure over night. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. To this concentrate formic acid (10 ml) was added and the resulting solution was stirred at 80° C. over night. Excess formic acid was removed by evaporation. The residue was dissolved in water and rendered alkaline by addition of solid sodium carbonate. Extraction with ethyl acetate and treatment of the extract with activated carbon in ethanol afforded 5-acetyl-1-[3-(1-methylpiperidin-3-yl)phenyl]-benzimidazole (9) (0.5 g, 50%) as an oil. m/e 333.

Aufarbeitung

  1. waitthe mixture was hydrogenated at ambient pressure over night
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo this concentrate formic acid (10 ml) was added
  5. customExcess formic acid was removed by evaporation
  6. dissolutionThe residue was dissolved in water
  7. additionby addition of solid sodium carbonate
  8. extractionExtraction with ethyl acetate and treatment of the
  9. extractionextract with activated carbon in ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6a390e410e4a423d91c9e48f13705ebb
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503925B1

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