Benzylamine → 4-benzylamino-1H-imidazo(4,5-c)pyridine

HRID 1979525Notes

Reaction equation

HRID 1979525 reaction equation
Cl[C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[CH2:11]([NH:18][C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridine

Product 1

HCID 131316894-benzylamino-1H-imidazo(4,5-c)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-chloro-1H-imidazo-[4,5-c]-pyridine (2.0 g, 13 mmole), benzylamine (5 ml) and a few drops of water was heated at reflux for 4 days. The reaction mixture was poured onto ice and water and the cold mixture was extracted twice with diethylether. The ether was removed in vacuo and the residual oil was triturated twice with hexane. The oil was suspended in water and the aqueous phase was neutralised with glacial acetic acid. The aqueous phase was taken to dryness in vacuo and resuspended in water (15 ml). It was applied to a column of Dowex 50 (H+) (10 g). The column was washed with water until the ultra violet absorbance of the eluant had fallen to zero. The column packing was removed from the column and heated with several portions of concentrated ammonium hydroxide solution (400 ml). The basic solution was filtered in vacuo, cooled and neutralized with glacial acetic acid. The yellow solid was collected and dried in vacuo at 40° C. Yield of 4-benzylamino-1 H-imidazo-[4,5-c]-pyridine 0.94 g, m.p. 60°-64° C., 31.5%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. extractionthe cold mixture was extracted twice with diethylether
  4. customThe ether was removed in vacuo
  5. customthe residual oil was triturated twice with hexane
  6. washThe column was washed with water until the ultra violet absorbance of the eluant
  7. customThe column packing was removed from the column
  8. temperatureheated with several portions of concentrated ammonium hydroxide solution (400 ml)
  9. filtrationThe basic solution was filtered in vacuo
  10. temperaturecooled
  11. customThe yellow solid was collected
  12. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-59573f0b39cd4d768c63ee59afa3459c
Source dataset
uspto-grants-1984_11
Patent number
US04481197

Reaction notes

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