Ethyl bromoacetate → HCID 54510475, compound

HRID 1588237Notes

Reaction equation

HRID 1588237 reaction equation
N[CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.C([N:11](CC)CC)C.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>O1CCCC1>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:11][C:4]1[C:3]([CH3:2])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 310183-Pyridinemethanamine

Product 1

HCID 54510475HCID 54510475, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Aminomethylpyridine (21.6g, 0.2 mol) and equal molar triethylamine (20.2 g) were dissolved in tetrahydrofuran and cooled by means of an ice water bath to 0°-5° C. Ethyl bromoacetate (33.4 g, 0.2 mol) was added dropwise to the solution where by a suspension formed. The mixture was allowed to stir at room temperature over the weekend. The solvent was concentrated under vacuum. The residue was treated with water and extracted into ethyl acetate. The organic extract was washed repeatedly with water and dried over magnesium sulfate. After filtering from the drying agent the solvent was concentrated and the residue was treated with anhydrous ether. The cloudy solution was filtered through a pad of Celite and afterwards cooled to 0° C. with an ice bath. Slow addition of ether which had previously been saturated with anhydrous hydrogen chloride resulted in the product to precipitate as the HCl-salt. The solid product was filtered and washed with ether to give 15.0 g of a hygroscopic material with a melting point of 125°-127° C.

Workup

  1. temperaturecooled by means of an ice water bath to 0°-5° C
  2. customformed
  3. concentrationThe solvent was concentrated under vacuum
  4. additionThe residue was treated with water
  5. extractionextracted into ethyl acetate
  6. extractionThe organic extract
  7. washwas washed repeatedly with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtering from the drying agent the solvent
  10. concentrationwas concentrated
  11. additionthe residue was treated with anhydrous ether
  12. filtrationThe cloudy solution was filtered through a pad of Celite
  13. temperatureafterwards cooled to 0° C. with an ice bath
  14. additionaddition of ether which
  15. customresulted in the product
  16. customto precipitate as the HCl-salt
  17. filtrationThe solid product was filtered
  18. washwashed with ether

Sources & evidence

ORD record
ord-e4f1d1857cd74ce987519027c2dfb23e
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

Loading…