N-Methylbenzylamine → 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole

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A mixture of 800 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 720 mg of N-methylbenzylamine and 1.0 g of triethylamine in 5 ml of DMF was stirred at room temperature for 8 hours. The reaction mixture was then poured into ice-water and the resultant mixture was extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to yield a brown oil. Chromatography on silica gel using chloroform-methanol (20:1, v/v) as eluent afforded 780 mg of 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole as a colorless oil, IR νmaxneat cm-1 : 1730, 1635, 1580, 1545, 1450, 1360.

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