4-Azidomethyl 1-(4-iodophenyl)imidazole → 4-Aminomethyl 1-(4-iodophenyl)imidazole

HRID 1802575Notes

Reaction equation

HRID 1802575 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:9]=1)=[N+]=[N-]>CO.[Ni]>[NH2:1][CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 592600984-Azidomethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 592601094-Aminomethyl 1-(4-iodophenyl)imidazoleYield 90.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-azidomethyl 1-(4-iodophenyl)imidazole 1-4 (0.725 g, 2.23 mmol) over Ra—Ni (50% aq. slurry, 300 mg) in MeOH (12 mL) was hydrogenated under balloon H2 for 3 h. The mixture was filtrated through CELITE. The filtrate was concentrated in vacuo to give 4-aminomethyl 1-(4-iodophenyl)imidazole 1-2 as a solid (0.603 g). MS 300.0 (M+H)

Workup

  1. filtrationThe mixture was filtrated through CELITE
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d319003c519a4ff6b020f9b980906250
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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