Hydrochloric Acid → HCID 15337836, compound

HRID 651894Notes

Reaction equation

HRID 651894 reaction equation
[CH2:1]([NH2:5])/[CH:2]=[CH:3]/[CH3:4].Cl.Br[CH2:8][C:9]([O:11][CH3:12])=[O:10].CCN(CC)CC>C(#N)C>[CH2:1]([NH:5][CH2:8][C:9]([O:11][CH3:12])=[O:10])/[CH:2]=[CH:3]/[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 643377221035-54-1

Product 1

HCID 15337836HCID 15337836, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of (E)-2-buten-1-amine.HCl (5.37 g, 49.9 mmol) (Chem. Ber., 1984;117:1250) in acetonitrile (100 mL) was treated with methyl bromoacetate (4.72 mL, 49.9 mmol) and Et3N (14.0 mL, 99.8 mmol) and stirred at room temperature for 1 hour. The suspension was then heated at reflux overnight. Solution occurred at reflux temperature. After cooling, the precipitated Et3NHCl was filtered off and the solvent removed under reduced pressure leaving 5.0 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98:2) gave 1.41 g (19.8% yield) of the pure product as an oil.

Workup

  1. temperatureThe suspension was then heated
  2. temperatureat reflux overnight
  3. temperatureat reflux temperature
  4. temperatureAfter cooling
  5. filtrationthe precipitated Et3NHCl was filtered off
  6. customthe solvent removed under reduced pressure
  7. customleaving 5.0 g of the crude product
  8. washChromatography on silica gel, eluting with CHCl3/MeOH (98:2)

Sources & evidence

ORD record
ord-fc24858ec371475b9ebfcebea50de4dd
Source dataset
uspto-grants-2001_08
Patent number
US06281194B1

Reaction notes

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