Ethyl Acetate → (S)-3-(3-chloro-phenyl)-N1,N1-dimethyl-propane-1,2-diamine hydrochloride salt

A solution of lithium aluminum hydride in tetrahydrofuran (3.5 M; 20 mL; 70 mmol) was added cautiously to an ice-bath cooled solution of (S)-2-amino-3-(3-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt (4.00 g, 11.8 mmol) in tetrahydrofuran (20 mL). The reaction mixture was heated at reflux for 4 h, and then cooled. Ethyl acetate and ether were added, and then 3 M sodium hydroxide solution (100 mL) was added. The layers were separated and the aqueous layer was back-extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was taken up in 1 M HCl in ether (20 mL). The resulting white precipitate was stirred for 1 h, and then filtered to give (S)-3-(3-chloro-phenyl)-N1,N1-dimethyl-propane-1,2-diamine hydrochloride salt (1.92 g, 57%).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 4 h
3. temperaturecooled
4. customThe layers were separated
5. extractionthe aqueous layer was back-extracted with ether
6. washThe combined organic layers were washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customevaporated
10. filtrationfiltered

ORD record

ord-b2b202aeca494a449ec4b39e4c4212ac

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314250B2