Hydrochloric Acid → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-hydroxyphenyl)-3-phenylacrylamide

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Reaction Steps

To a solution of 8 (70 mg, 0.144 mmol) in MeOH (3 ml) was added 4N HCl in 1,4-dioxane (0.4 ml) under ice cooling, and the mixture was stirred at room temperature for 3 h. A solution of NaHCO3 in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was crystallized with Et2O to give 9 (88%). 9: colorless powder; 1H-NMR (CD3OD) δ 0.42 (2H, m), 0.73 (2H, m), 1.99 (1H, m), 2.35 (6H, s), 2.77 (2H, t, J=5.4 Hz), 4.10 (2H, t, J=5.4 Hz), 6.47 (2H, d, J=8.8 Hz), 6.91 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.1 Hz), 7.06 (2H, m), 7.13-7.23 (3H, m), 7.56 (2H, d, J=9.3 Hz). HRMS calcd for C28H31N2O3 [M+H]+: 443.2335. Found: 443.2353.

Provenance & Evidence