Benzylamine → Lacosamide EP Impurity E

To a stirred methanolic solution (250 mL) of L-serine methyl ester hydrochloride ((S)-6) (20.00 g, 128 mmol) was added benzylamine (55.9 mL, 512 mmol), and then the reaction solution was heated at reflux (18 h). The solvent was removed under reduced pressure, the insoluble salts were filtered, and the excess benzylamine was removed under high vacuum (Kugelrohr). The residue was dissolved in H2O (100 mL), and the product was extracted with CHCl3 (8×200 mL). The organic layers were combined and dried (Na2SO4), and the solvent was removed under reduced pressure. The residue was triturated with Et2O (150 mL) and filtered to give 8.50 g (34%) of the product as a white solid: mp 76-80° C.

1. temperaturethe reaction solution was heated
2. temperatureat reflux (18 h)
3. customThe solvent was removed under reduced pressure
4. filtrationthe insoluble salts were filtered
5. customthe excess benzylamine was removed under high vacuum (Kugelrohr)
6. dissolutionThe residue was dissolved in H2O (100 mL)
7. extractionthe product was extracted with CHCl3 (8×200 mL)
8. dry with materialdried (Na2SO4)
9. customthe solvent was removed under reduced pressure
10. customThe residue was triturated with Et2O (150 mL)
11. filtrationfiltered

ORD record

ord-bda47d887d0c4c28a3956a75f2fc1e5c

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133261