Xylometazoline → Xylometazoline metabolite

HRID 1595456

Reaktionsgleichung

Reaktionsgleichung von HRID 1595456
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[C:7]([CH3:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[C:7]([CH3:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 5709Xylometazoline

Produkt 1

HCID 557409Xylometazoline metaboliteAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]4,5dihydro-1H-imidazole (free base of Example 5c) (0.1 g, 0.4 mmol) and 10% Pd-C (0.1 g) in toluene (10 mL) was refluxed under a nitrogen atmosphere for 3 days. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole (0.085 g) as a white solid. The oxalate salt was prepared and recrystallized from MeOH/Et2O to afford the title compound as white crystals (0.088 g, 66%). mp 154-156° C., Anal. C16H22N2.C2H2O4: C, H, N.

Aufarbeitung

  1. temperaturewas refluxed under a nitrogen atmosphere for 3 days
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83c3940320bc42f9900bfbf9dda4fa00
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288101B1

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