Dibenzylamine → Ethyl 2-(dibenzylamino)acetate

Ethyl bromoacetate (19.52 mL, 176 mol) was added in a single portion to a chilled (0° C.) solution of dibenzylamine (33.84 mL, 176 mmol) and triethylamine (27 mL, 193.6 mmol) in THF. The reaction mixture was stirred overnight at ambient temperature. Additional triethylamine (30 mL) and THF (100 mL) were added and the reaction mixture was heated at 50° C. for 1.5 hours. Additional ethyl bromoacetate (13 mL) was added and the reaction mixture was heated for 1 hour and then stirred at ambient temperature overnight. About half of the THF was removed under reduced pressure. The mixture was diluted with water (300 mL) and then extracted with ethyl acetate (2×400 mL). The combined extracts were washed sequentially with water and with brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography (700 g of silica gel, eluting with 20% ethyl acetate in hexanes) to provide 37.12 g of ethyl dibenzylaminoacetate as a colorless oil.

1. temperaturethe reaction mixture was heated at 50° C. for 1.5 hours
2. temperaturethe reaction mixture was heated for 1 hour
3. stirringstirred at ambient temperature overnight
4. customAbout half of the THF was removed under reduced pressure
5. additionThe mixture was diluted with water (300 mL)
6. extractionextracted with ethyl acetate (2×400 mL)
7. washThe combined extracts were washed sequentially with water and with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography (700 g of silica gel, eluting with 20% ethyl acetate in hexanes)

ORD record

ord-c7beeeff11764e9cad9be4fb9ed5b64e

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884207B2