Chloroacetyl chloride → 2-Chloro-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-acetamide

4.5 ml of triethylamine were added to a solution of 5.11 g of 2-(3,4-dimethoxyphenyl)ethylamine dissolved in 35 ml of methylene chloride, and the mixture was stirred, whilst ice-cooling. 2.4 ml of chloroacetyl chloride were then added dropwise to the mixture over a period of 5 minutes, after which the mixture was stirred for 15 minutes, whilst ice-cooling. The reaction mixture was then concentrated by evaporation under reduced pressure, and ethyl acetate was added to the resulting residue. The ethyl acetate solution was washed, in turn, with water, with a 5% w/v aqueous solution of sodium bicarbonate, with 10% w/v aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride. It was then dried, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and hexane, to give 5.77 g of the title compound as pale yellow-brown, feather-like crystals melting at 92-94° C.

1. temperaturecooling
2. stirringafter which the mixture was stirred for 15 minutes, whilst ice-
3. temperaturecooling
4. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure, and ethyl acetate
5. additionwas added to the resulting residue
6. washThe ethyl acetate solution was washed, in turn, with water, with a 5% w/v aqueous solution of sodium bicarbonate, with 10% w/v aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride
7. customIt was then dried
8. distillationthe solvent was distilled off under reduced pressure
9. customThe residue was recrystallized from a mixture of ethyl acetate and hexane

ORD record

ord-77266fb5fe3040fa86a51045ba268f43

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04898862