Hydrochloric Acid → tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamate

Participants

Reaction Steps

A solution of tert-butyl N-(2-aminoethyl)carbamate (1.00 g, 6.24 mmol) and 4-chlorobenzaldehyde (0.90 g, 6.37 mmol) in DCE (10 mL) was stirred for 30 minutes, followed by the addition of NaBH(OAc)3 (1.98 g, 9.36 mmol) in a single portion. After being stirred for 12 hours, the mixture was acidified to pH 2 with 0.2N HCl, and extracted with DCM (3 times, each discarded). The acidic aqueous layer was basified to pH 10 with 2.0 M NaOH, and extracted with DCM. The DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give [2-(4-chlorobenzylamino)-ethyl]-carbamic acid tert-butyl ester as an oil (1.0 g). LCMS (APCI+) m/z 285, 287 [M+H]+.

Provenance & Evidence