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

HRID 67944Notes

Reaction equation

HRID 67944 reaction equation
Cl[N:2]1[C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:4]=[CH: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:6]1[C:5]2[N:4]=[CH:3][NH:2][C:10]=2[CH:9]=[CH:8][N:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 19388379chloro-1H-imidazo(4,5-c)pyridine

Product 1

HCID 131316894-benzylamino-1H-imidazo(4,5-c)pyridineYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 962WaterSolvent

Procedure

A mixture of chloro-1H-imidazo(4,5-c)pyridine (2.0 g, 13 mmol), 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 diethyl ether. 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) and applied to a column of Dowex 50 (H+) resin (10 g). The column was washed with water until the ultra violet absorbance of the eluant was 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. to give 4-benzylamino-1H-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 diethyl ether
  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-ddf94e74fc314a61a69dc63c61f26ab5
Source dataset
uspto-grants-1982_08
Patent number
US04347315

Reaction notes

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