2-[4-(2-Azidoethyl)phenyl]-1H-imidazole → 2-[4-(1H-Imidazol-2-yl)phenyl]ethan-1-amine

HRID 1071968Notes

Reaction equation

HRID 1071968 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)=[CH:8][CH:7]=1)=[N+]=[N-].[H][H]>CCO.[Pd]>[NH:13]1[CH:14]=[CH:15][N:16]=[C:12]1[C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][NH2:1])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 223907362-[4-(2-Azidoethyl)phenyl]-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 223906912-[4-(1H-Imidazol-2-yl)phenyl]ethan-1-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[4-(2-azidoethyl)phenyl]-1H-imidazole (120 mg, 0.56 mmol) in EtOH, Pd/C (6 mg, 0.06 mmol) was added. A hydrogen balloon was placed over the reaction and the reaction was complete after approximately five hours. Reaction mixture was filtered through a pad of celite and concentrated to give 2-[4-(1H-imidazol-2-yl)phenyl]ethanamine which was used without further purification. LCMS (ES) m/z 188.4 (M+H)+.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d30bfff6a16441bdb9531b173e7ecbf5
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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