Sodium Chloride → 3-(1H-1,3-benzodiazol-1-yl)propan-1-amine

HRID 1388907Notes

Reaction equation

HRID 1388907 reaction equation
[N:1]1([CH2:10][CH2:11][C:12]#[N:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[H][H].[Cl-].[Na+]>[Ni].C(O)C.O>[N:1]1([CH2:10][CH2:11][CH2:12][NH2:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 29985553-(1H-benzimidazol-1-yl)propanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 39208493-(1H-1,3-benzodiazol-1-yl)propan-1-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4.2 Grams of 1H-benzimidazole-1-propionitrile, 0.2 grams sodium hydroxide, 1 gram of Raney nickel catalyst in about 100 ml of ethanol was hydrogenated at room temperature and atmospheric pressure for about 20 hours. The hydrogen uptake had stopped by this time with a total uptake of about 1300 ml. The reaction mixture was filtered and the catalyst was washed first with ethanol and then with water. The filtrates were combined and the solvent evaporated to leave a yellowish oil. The oil was dissolved in water, the water was saturated with sodium chloride, and the mixture was extracted with three portions of methylene chloride. The methylene chloride extracts were combined, washed with sodium chloride solution and then dried over potassium carbonate. The mixture was then filtered and the solvent evaporated to leave yellowish oil which was then distilled to give 1H-benzimidazole-1-propanamine boiling at 167°-170° C. at 1-1.3 mm pressure.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe catalyst was washed first with ethanol
  4. customthe solvent evaporated
  5. customto leave a yellowish oil
  6. extractionthe mixture was extracted with three portions of methylene chloride
  7. washwashed with sodium chloride solution
  8. dry with materialdried over potassium carbonate
  9. filtrationThe mixture was then filtered
  10. customthe solvent evaporated
  11. customto leave yellowish oil which
  12. distillationwas then distilled

Sources & evidence

ORD record
ord-e797c7d801474c14b3b6456ecc760d7c
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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