Benzaldehyde → N-Benzyl-beta-alanine

HRID 1428421Notes

Reaction equation

HRID 1428421 reaction equation
Cl.C([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])C.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH2:10]([NH:8][CH2:7][CH2:6][C:5]([OH:4])=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 225173N-Benzyl-beta-alanineYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ten grams of β-alanine ethyl ester hydrochloride and 9 g of benzaldehyde were added to 100 mL of toluene and heated and refluxed using a Dean-Stark trap. After heating and stirring for three hours, the product was cooled in air, and the reaction system was concentrated under reduced pressure. 200 mL of ethanol were added to the resulting residue, and 5 g of sodium borohydride were added while stirring under freezing conditions. After stirring over a period of one night, hydrochloric acid was added and the pH was brought to 2 or less. After filtering, the product was concentrated under reduced pressure, the resulting residue was dissolved in 200 mL THF-water, and 2 g of sodium hydroxide were added. After stirring for six hours at room temperature, the product was neutralized with Amberlite IR120B[H] and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized to obtain 8.2 g f the desired product (yield of 70%).

Workup

  1. temperatureheated
  2. temperaturerefluxed
  3. temperatureAfter heating
  4. temperaturethe product was cooled in air
  5. concentrationthe reaction system was concentrated under reduced pressure
  6. addition200 mL of ethanol were added to the resulting residue, and 5 g of sodium borohydride
  7. additionwere added
  8. stirringwhile stirring under freezing conditions
  9. stirringAfter stirring over a period of one night
  10. additionhydrochloric acid was added
  11. filtrationAfter filtering
  12. concentrationthe product was concentrated under reduced pressure
  13. dissolutionthe resulting residue was dissolved in 200 mL THF-water
  14. addition2 g of sodium hydroxide were added
  15. stirringAfter stirring for six hours at room temperature
  16. filtrationfiltered
  17. concentrationthe filtrate was concentrated under reduced pressure
  18. customThe resulting residue was recrystallized

Sources & evidence

ORD record
ord-16426783f91a4760ada7b2a568ed99ce
Source dataset
uspto-grants-2015_01
Patent number
US08937090B2

Reaction notes

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