Gamma-Aminobutyric Acid → 4-Aminobutyrate ethyl hydrochloride

Ethanol (500 mL) was cooled to 0° C., and thionyl chloride (85 mL, 1.2 mol) was added dropwise with stirring. The reaction was stirred for one hour at 0° C., and solid 4-aminobutyric acid (100 g, 0.97 mol) was then added. After ten minutes of stirring, the reaction was allowed to warm to ambient temperature and stirred for two hours. The reaction was then allowed to stand at ambient temperature overnight. The ethanol was removed under reduced pressure, and the solid residue was dissolved in ethyl acetate. After one hour, the solution was cooled to 0° C., and a precipitate formed. The precipitate was isolated by filtration and washed with diethyl ether (300 mL) to provide 126.6 g of ethyl 4-aminobutyrate hydrochloride as a white solid. A precipitate formed in the filtrate and was isolated by filtration to provide 19.1 g of ethyl 4-aminobutyrate hydrochloride as a white solid.

1. stirringThe reaction was stirred for one hour at 0° C.
2. stirringAfter ten minutes of stirring
3. stirringstirred for two hours
4. customThe ethanol was removed under reduced pressure
5. dissolutionthe solid residue was dissolved in ethyl acetate
6. waitAfter one hour
7. temperaturethe solution was cooled to 0° C.
8. customa precipitate formed
9. customThe precipitate was isolated by filtration
10. washwashed with diethyl ether (300 mL)

ORD record

ord-1f534bea5d8e4a16aee60ffc625fca48

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697873B2