2-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine → 3-[1-Acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole

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The mixture of 2-acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine (1.5 g) and molecular sieves 4A (7.5 g) in dioxane (50 ml) was refluxed for 2 hours. After molecular sieves were removed by filtration, the filtrate was evaporated in vacuo. The residue was chromatographed on silica eluting with 3% methanol in chloroform to give 3-[1-acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole (0.63 g, 43.6%). The compound (74 mg) was dissolved in a solution of fumaric acid (18 mg) in ethanol to give 3-[1-acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole fumarate (80 mg).

Provenance & Evidence