4-azidomethyl-5-methyl-2-phenyl-1H-imidazole → C-(5-methyl-2-phenyl-1H-imidazol-4-yl)-methylamine

HRID 2249607Notes

Reaction equation

HRID 2249607 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:9]=1[CH3:10])=[N+]=[N-]>C(O)C.[Pd]>[CH3:10][C:9]1[NH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 225633704-azidomethyl-5-methyl-2-phenyl-1H-imidazole

Product 1

HCID 22563473C-(5-methyl-2-phenyl-1H-imidazol-4-yl)-methylamineYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To solution of 4-azidomethyl-5-methyl-2-phenyl-1H-imidazole (1.22 g) in ethanol (50 ml) was added 10% Pd/C (0.10 g). The reaction mixture was hydrogenated at room temperature and 1.1 bar for 30 minutes, the catalyst was filtered off over a pad of celite. The filtrate was evaporated to dryness under high vacuum to obtain C-(5-methyl-2-phenyl-1H -imidazol-4-yl)-methylamine (1.06 g) as a light yellow foam which was sufficiently pure to be used directly in the next step.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe catalyst was filtered off over a pad of celite
  3. customThe filtrate was evaporated to dryness under high vacuum

Sources & evidence

ORD record
ord-6603af40456c457595ffd4fc9adc112a
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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