Synthesis and Crystal Structure of the Derivative of Hydroquinone from Mannich Reaction

The regioselective Mannich-type aminomethylation of hydroquinone afforded a nitrogen-containing compound, 2,5-bis-(morpholinomethyl)hydroquinone A, and its crystal structure was determined by single-crystal X-ray diffraction. Crystal data for A: C16H24N2O4, Mr = 308.37, orthorhombic, space group Pbca, a = 10.479(4), b = 10.298(4), c = 14.865(5) (A), V = 1604.3(11) (A)3, Z = 4, Dc = 1.277 g/cm3, F(000) = 664, μ = 0.092 mm-1, GOF = 1.078, the final R = 0.0508 and wR = 0.1075 for 1416 observed reflections with I > 2σ(I). There exist two intramolecular O-H...N hydrogen bonds between the phenolic O atoms and the morpholine N donors and the morpholino rings assume the preferred chair conformation.