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

Participants

Reaction Steps

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%).

Provenance & Evidence