Formic Acid → 3-(4-Isopropylpiperazin-1-yl)-5-(trifluoromethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Water (1.3 mL) was added to a suspension of 1-(3-(1,3-dioxolan-2-yl)-5-(trifluoromethoxy)phenyl)-4-isopropylpiperazine (22, 996 mg, 2.76 mmol) and formic acid (6.71 g, 145 mmol). The mixture was heated to 60° C. for 20 h. The reaction mixture was concentrated to a brown oil in vacuo. The oil was dissolved in EtOAc (100 mL) and the solution was washed with saturated aq. NaHCO3 solution (100 mL) and brine (100 mL). After drying over Na2SO4, the suspension was filtered and the filtrate concentrated to an orange oil. The residue was purified by silica gel chromatography eluting with 0-80% EtOAc in hexanes to afford the title compound (608 mg, 70%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 9.92 (s, 1H), 6.93 (s, 1H), 7.31 (s, 1H), 7.13 (s, 1H), 6.92 (s, 1H), 3.30-3.28 (m, 4H), 2.73 (sept, 1H), 2.70-2.64 (m, 4H), 1.10 (d, J=6.5 Hz, 6H).

Provenance & Evidence