4-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile → 4-(3-Amino-1-imidazol-1-yl-propyl)-benzonitrile

HRID 1421781Notes

Reaction equation

HRID 1421781 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][CH:6]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

4

Reactant 1

HCID 187797504-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile

Product 1

HCID 187797234-(3-Amino-1-imidazol-1-yl-propyl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 4-(3-azido-1-imidazol-1-yl-propyl)-benzonitrile (490 mg, 1.9 mmol) was suspended in methanol (20 mL) and placed under argon. 10% Palladium on Carbon catalyst was carefully added under argon and the solution was evacuated under vacuum to bubbling and then purged with argon 3 times. The suspension was evacuated again and then a balloon filled with hydrogen was opened to the reaction. The reaction was left under hydrogen at room pressure for 16 hours. The reaction was evacuated again to bubbling and purged with argon. The catalyst was filtered off through a bed of celite under argon. The supernatant was concentrated in vacuo to give the desired product.

Workup

  1. customthe solution was evacuated under vacuum
  2. customto bubbling
  3. custompurged with argon 3 times
  4. customThe suspension was evacuated again
  5. additiona balloon filled with hydrogen
  6. customwas opened to the reaction
  7. customThe reaction was evacuated again
  8. customto bubbling
  9. custompurged with argon
  10. filtrationThe catalyst was filtered off through a bed of celite under argon
  11. concentrationThe supernatant was concentrated in vacuo

Sources & evidence

ORD record
ord-d8aef07b022d4139aae622c3c65481d4
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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