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

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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, 4H), 3.42 (t, J=5.6 Hz, 4H), 3.91 (s, 4H), 4.89 (s, 2H), 6.97 (d, J=9.0 Hz, 2H), 7.30-7.50 (m, 5H), 7.62 (d, J=9.0 Hz, 2H); MS (ES) m/z: 369.3 (MH+); HRMS Calcd. for C21H24N2O4 (M+): 368.1736. Found: 368.1744.

Provenance & Evidence