HCID 58709769, compound → HCID 58710088, compound

HRID 2375910Notes

Reaction equation

HRID 2375910 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)=[CH:8][N:7]=[CH:6]1.[H][H]>CO.[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 2

HCID 58709769HCID 58709769, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58710088HCID 58710088, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of dimethyl-{2-[5-(3-nitrophenyl)imidazol-1-yl]ethyl}amine (140 mg, 0.54 mmol) and 10% Pd/C (80 mg) in methanol (8 mL) was hydrogenated under 1 atm hydrogen pressure for 5 h. The reaction mixture was filtered through a Celite pad. The filtrate was concentrated to dryness to afford the desired amine, which was used directly in the next step without purification. 1H-NMR (CD3OD, 400 MHz): δ=2.15 (s, 6H), 2.49 (t, J=6.8 Hz, 2H), 4.18 (t, J=7.2 Hz, 2H), 6.69-6.77 (m, 3H), 6.91 (d, J=1.2 Hz, 1H), 7.18 (dt, J=1.2, 7.6 Hz, 1H), 7.44 (d, J=0.8 Hz, 1H). MS (ES+): m/z 231.29 [MH+]. HPLC: tR=0.39 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-1b46fa375e14411085f96c4d3d40c08b
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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