Trifluoroacetic acid → (S)-1-(4-Chloro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

Participants

Reaction Steps

To a solution of [(S)-1-(4-chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.40 g, 3.76 mmol) in DCM (20 mL) was added TFA (20 mL) and the resulting mixture was stirred at RT for 20 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous layer was further extracted with DCM and the combined organic layers were then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) affording (S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a white solid (680 mg, 67%). LCMS: RT 2.23 min [M+H]+ 272.1

Provenance & Evidence