4-Methylmorpholine → N-(Benzyloxy)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzamide

Participants

Reaction Steps

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid (which was obtained in Example 150) (1.58 g, 6 mmol), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.34 g, 7 mmol) and O-benzylhydroxyamine hydrochloride (1.05 g, 6.6 mmol) was stirred in methylene chloride (150 mL). N-methylmorpholine (1.82 g, 18 mol) was added dropwise and the mixture was stirred overnight. The mixture was then washed with 0.05 N hydrochloric acid and water. The resulting solution was dried with magnesium sulfate and concentrated. The residue was crystallized from methylene chloride/hexanes to give the title compound as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.67 (t, J=5.6 Hz, 4 H), 3.42(t, J=5.6 Hz, 4 H), 3.91(s, 4 H), 4.89(s, 2 H), 6.97 (d, J=9.0 Hz, 2 H), 7.30–7.50(m, 5 H), 7.62 (d, J=9.0 Hz, 2 H); MS (ES) m/z: 369.3 (MH+); HRMS Calcd. for C21H24N2O4(M+): 368.1736. Found: 368.1744.

Provenance & Evidence