Benzylamine → Aplindore

Participants

Reaction Steps

A 25 mL, flask is charged with [(2R)-8-oxo-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-2-yl]methyl 4-methylbenzenesulfonate (1.00 g, 2.7 mmol) and DMSO (8.0 mL). Nitrogen gas is bubbled through the solution for 10 min, benzylamine (0.73 mL, 6.7 mmol) is added and nitrogen is bubbled through the mixture for another 15 min. The flask is immersed in an 85° C. oil bath and stirred for 18 h. The solution is cooled, water (24 mL) is added and the resulting solution is extracted with MTBE (3×15 mL). The combined organic extracts are washed successively with water (10 mL), saturated NH4Cl (10 mL) and saturated NaHCO3 (10 mL), and are evaporated to give the crude title compound (0.85 g, 101%) as a red syrup. LCMS (Basic Method): 1.84 min, 311 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 10.4 (br s, 1H), 7.35-7.27 (m, 5H), 6.73 (d, J=8.3 Hz, 1H), 6.36 (d, J=8.3 Hz, 1H), 4.37-4.35 (m, 1H), 4.25 (dd, J=2.2, 11.5 Hz, 1H), 4.03 (dd, J=7.3, 11.5 Hz, 1H), 3.88 (s, 2H), 3.44 (s, 2H), 2.97-2.88 (m, 2H), 8.9 (br s, 1H).

Provenance & Evidence