Triethylamine → HCID 15337836, compound

HRID 841146Notes

Reaction equation

HRID 841146 reaction equation
Cl.[CH2:2]([NH2:6])/[CH:3]=[CH:4]/[CH3:5].Br[CH2:8][C:9]([O:11][CH3:12])=[O:10].CCN(CC)CC>C(#N)C>[CH2:2]([NH:6][CH2:8][C:9]([O:11][CH3:12])=[O:10])/[CH:3]=[CH:4]/[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 12602976209907-25-5

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. 117, 1250(1984) 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 I hour. The suspension was then heated at reflux overnight. Solution occurred at reflux temperature. After cooling, the precipitated Et3N.HCl 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 Et3N.HCl 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-b48ead47966248b78789211493f77817
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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