1-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine → 1-benzoyl-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine

HRID 1904824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904824
[C:1]([N:9]1[CH:14]=[CH:13][CH:12]([CH2:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[C:1]([N:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)=[CH:13][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 145180941-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 200379061-benzoyl-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridineAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 16 parts of 1-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine and 160 parts of methanol was hydrogenated at normal pressure and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The oily residue was crystallized from 14 parts of 1,1'-oxybisethane. The product was filtered off and dried, yielding 7.8 parts (58.5%) of 1-benzoyl-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine; mp. 159.3° C. (32).

Aufarbeitung

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe oily residue was crystallized from 14 parts of 1,1'-oxybisethane
  8. filtrationThe product was filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b76ae46e401845598f01e357c0f225b2
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04839374

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