Dimethylamine, hydrochloride → (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N,N-dimethylamino) phenyl)piperazine

Participants

Reaction Conditions

Reaction Steps

A suspension of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl) piperazine (1.14 g, 2.59 mmol), N,N-dimethylamine hydrochloride (422 mg, 5.17 mmol), palladium acetate (23 mg, 0.10 mmol), 2-(di-t-butylphosphino)biphenyl(62 mg, 0.21 mmol), and sodium t-butoxide (845 mg, 8.80 mmol) in t-butanol (15 mL) was heated at 90° C. for 3 h. After dilution with ethyl acetate, the resulting solution was passed through a Celite column. The filtrate was concentrated, and the residue was purified by silica gel column chromatography eluting 10-20% ethyl acetate-hexane to afford (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N,N-dimethylamino) phenyl)piperazine (556 mg, 53%) as white crystals.

Provenance & Evidence