Hydrochloric Acid → 8-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride

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Reaction Steps

A mixture of 1.7 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 2 g 2-(1-hydroxy-2-bromoethyl)-1,4-benzodioxane [J. Med. Chem., 13, 169 (1970)], 3 ml triethylamine and 5 ml N,N-dimethylformamide is heated at 90° for 18 hours. The mixture is poured into 100 ml water and the resulting mixture stirred for 10 minutes. The stirring is stopped and the aqueous layer decanted. The crude product is filtered through 20 g silica gel with 10% methanol-methylene chloride. Evaporation of the filtrate gives a residue which is taken up in 10 ml methanol. To this solution is added 10 ml of a 3% solution of hydrochloric acid in methanol. Addition of 200 ml of diethyl ether affords a precipitate which is collected by filtration, yielding 1.1 g (mixed erythro and threo) 8-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride, mp 235°-247° (d).

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