Sodium Hydroxide → 2-(4-Aminomethylphenyl)-4-phenyl-5-(4-pyridyl)-imidazole

HRID 1417085Notes

Reaction equation

HRID 1417085 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 154078722-(4-cyanophenyl)4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazoleHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 187715392-(4-Aminomethylphenyl)-4-phenyl-5-(4-pyridyl)-imidazoleYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-cyanophenyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole (2.5 g, 7.3 mmol) [See Ex. 96 above] in THF (50 mL) was added LiAlH4 (7.3 mL of 1M solution in THF, 7.3 mmol), and the resulting mixture was heated at reflux for 2 h, at which time tlc analysis indicated that the reaction was incomplete. Additional LiAlH4 (4.0 mL, 4.0 mmol) was added and heating was continued for 30 min. The mixture was allowed to cool, then poured into 2.5N NaOH and extracted with THF. The organic extract was washed with saturated aqueous NaCl and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 9:1 CHCl3 /MeOH, followed by 90:10:1 CHCl3 /MeOH/NH3. The material that was isolated was triturated with Et2O to afford the title compound (1.5 g, 60%): mp 214-215° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 h, at which time tlc analysis
  3. temperatureheating
  4. temperatureto cool
  5. extractionextracted with THF
  6. extractionThe organic extract
  7. washwas washed with saturated aqueous NaCl
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography
  10. washeluting with 9:1 CHCl3 /MeOH
  11. customThe material that was isolated
  12. customwas triturated with Et2O

Sources & evidence

ORD record
ord-3b19046df8df49fdb44d74774d594d7c
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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