Acetic Acid → HCID 58976363, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [(1-ethoxycyclopropyl)oxy]trimethylsilane (4.5 mL. 22.4 mmol, 2 eq.), 1-(4-nitrophenyl)piperazine (2.32 g, 11.1 mmol, acetic acid (6.4 mL, 5 eq.), molecule sieves (3 A, 5 g), and sodium cyanoborohydride (2.1 g, 33.3 mmol, 3 eq.) in dry methanol (50 mL) is heated at 60-65° C. for 4 h. The reaction mixture is filtered, and the filtration is evaporated. The residue is dissolved in DCM (200 mL) and the resulting solution is washed with 2 N NaOH (100 mL), brine (100 mL×2), dried over MgSO4, and evaporated to provide a yellow solid (2.75 g, 100%). The compound is used in the next reaction without further purification. 1H NMR (300 MHz, DMSO-d6), δ 8.02 (d, J=9.6 Hz, 2H), 7.00 (d, J=9.6 Hz, 2H), 3.38-3.42 (m, 4H), 2.60-2.68 (m, 4H), 1.60-1.67 (m, 1H), 0.40-0.46 (m, 2H), 0.35-0.38 (m, 2H). LCMS-ESI (m/z): calcd for C13H17N3O2, 247.1; [M+H]+ found, 248.4.

Provenance & Evidence