Xylometazoline → Xylometazoline metabolite

HRID 1955100

Reaction equation

HRID 1955100 reaction equation
[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]

Participants

4

Reactant 1

HCID 5709Xylometazoline

Product 1

HCID 557409Xylometazoline metaboliteYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-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.

Workup

  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

Sources & evidence

ORD record
ord-8784c0908dc7454786b550521c00b7a1
Source dataset
uspto-grants-2000_09
Patent number
US06124338

Linked notes

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