Hydrochloric Acid → 1H-Benzimidazole-1-butanamine

HRID 1388909Notes

Reaction equation

HRID 1388909 reaction equation
[N:1]1([CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Cl>[Pd].C(O)C>[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 130667534-(1H-Benzimidazol-1-yl)butanenitrile

Product 1

HCID 43794811H-Benzimidazole-1-butanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution was prepared from 8.9 grams of the nitrile and 150 ml of absolute ethanol, 0.8 grams of palladium on charcoal and 8 ml of concentrated hydrochloric acid were added, and the resulting mixture was hydrogenated at room temperature and pressure for 48 hours. The reaction mixture was then filtered, the solvent was evaporated from the filtrate, and the residue was treated with aqueous 2 N sodium hydroxide solution and extracted with chloroform. The chloroform solution was dried and then distilled to give 1H-benzimidazole-1-butanamine boiling at about 180°-186° C. at 1.2 mm pressure.

Workup

  1. additionwere added
  2. customwas hydrogenated at room temperature
  3. filtrationThe reaction mixture was then filtered
  4. customthe solvent was evaporated from the filtrate
  5. additionthe residue was treated with aqueous 2 N sodium hydroxide solution
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform solution was dried
  8. distillationdistilled

Sources & evidence

ORD record
ord-eafdd4da9be94c9489f644686084e4b6
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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