tert-Butyl piperazine-1-carboxylate → HCID 70975537, compound

Participants

Reaction Steps

tert-Butyl piperazine-1-carboxylate (62 mg, 0.33 mmol) was added to a solution of 2-(4-fluorophenyl)thiazole-4-carbaldehyde (70 mg, 0.34 mmol) in 1,2-dichloroethane (3 mL) at 0° C., followed by sodium triacetoxyborohydride (85 mg, 0.4 mmol). The reaction mixture was allowed to warm up to room temperature, stirred for 16 h and further heated to 50° C. for another 4 h. The reaction mixture was quenched with 10% aqueous NaHCO3 and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 35% EtOAc in petroleum ether) to afford tert-butyl 4-((2-(4-fluorophenyl)thiazol-4-yl)methyl)piperazine-1-carboxylate (82 mg, yield 64%). 1H NMR (300 MHz, CDCl3) δ 7.96-7.91 (dd, J=9.0 Hz, 5.3 Hz, 2H), 7.15-7.09 (m, 3H), 3.75 (s, 2H), 3.50-3.46 (m, 4H), 2.55-2.52 (m, 4H), 1.46 (s, 9H). MS (ESI) m/z: Calculated for C19H24FN3O2S: 377.16. found: 378.3 (M+H)+

Provenance & Evidence