1-[4-(2-azidoethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole → 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylamine

HRID 967818Notes

Reaction equation

HRID 967818 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:13]2[CH2:23][CH3:24])=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pd]>[CH2:23]([C:13]1[N:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][NH2:1])=[CH:11][CH:10]=2)[CH:16]=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:14]=1)[CH3:24]

Participants

4

Reactant 1

HCID 222913861-[4-(2-azidoethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole

Product 1

HCID 222913932-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylamineYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(2-azidoethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole (960 mg, 3.0 mmol) in methanol (50 mL) was added 10% Pd—C (50 mg). The resulting mixture was stirred for 4 h under hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated to afford 900 mg (94%) of the title compound as colorless amorphous: MS (ESI) m/z 292 [M+H]+1H-NMR (CDCl3) δ1.26 (2H, t, J=7.5 Hz), 2.72 (3H, q, J=7.7 Hz), 2.84 (2H, t, J=6.6 Hz), 3.01-3.06 (2H, br), 7.20-7.40 (9H, m), 7.81 (2H, dd, J=7.1, 1.2 Hz).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-34e080c2efdb4ac0a6f8bed88ce50e5e
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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