Sodium Acetate → HCID 178463863, compound

HRID 1087291Notes

Reaction equation

HRID 1087291 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH:7]([C:9]1[N:10]=[CH:11][NH:12][CH:13]=1)[CH3:8])[CH2:5]Cl.C([O-])(=O)C.[Na+]>[Pd].C(O)(=O)C>[NH:12]1[CH:13]=[C:9]([CH:7]([CH3:8])[CH:4]([NH2:3])[CH3:5])[N:10]=[CH:11]1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 178437194HCID 178437194, compound

Product 1

HCID 178463863HCID 178463863, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2 g (8.1 mmol) 2-amino-1-chloro-3-(1H-imidazol-4-yl)butane dihydrochloride, 1.3 g (16.2 mmol) sodium acetate and 100 ml 10% acetic acid, are hydrogenated over 0.5 g 10% palladium on activated carbon for 10 days at 10 bar and ambient temperature. The catalyst is removed by filtration and the filtrate brought to pH 1 by addition of concentrated hydrochloric acid. After evaporation the oily residue is dissolved in dry ethanol and inorganic material is removed by filtration. By addition of petrolether the title compound crystallizes as dihydrochloride. Recrystallization from methanol/acetonitrile yields 0.72 g (40.4%) [3-(1H-imidazol-4yl)but-2-yl]amine.2HCl.0.25 methanol as colorless crystals, melting point: 249°-254° C. (decomp.).

Workup

  1. customThe catalyst is removed by filtration
  2. additionthe filtrate brought to pH 1 by addition of concentrated hydrochloric acid
  3. customAfter evaporation the oily residue
  4. dissolutionis dissolved in dry ethanol
  5. custominorganic material is removed by filtration
  6. additionBy addition of petrolether the title compound
  7. customcrystallizes as dihydrochloride
  8. customRecrystallization from methanol/acetonitrile

Sources & evidence

ORD record
ord-fcaba1e92da14567bfbe4c38dbb7c4dc
Source dataset
uspto-grants-1991_07
Patent number
US05034539

Reaction notes

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