2-Chloro-N,N-dimethylethylamine → Ethanamine, 2-((1,3-dihydro-6-methyl-4-(phenylmethyl)furo(3,4-c)pyridin-7-yl)oxy)-N,N-dimethyl-, dihydrochloride

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Reaction Steps

12.1 g (50 mmoles) of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol (compare Example 8, stage 1) are suspended in 40 ml of dry dimethylsulfoxide and converted to the sodium salt by adding 1.75 g (60 mmoles) of sodium hydride (85% strength in oil) at 20° C. When the evolution of hydrogen has ceased, 8.1 g (75 mmoles) of freshly distilled β-dimethylaminoethyl chloride are added dropwise, and the mixture is left to stand for 15 hours at 10° C. The dimethylsulfoxide is then distilled off under greatly reduced pressure. The residue is taken up in methylene chloride, the salts and the unconverted pyridinol are washed out with dilute sodium hydroxide solution and the organic phase is dried and concentrated under reduced pressure. The residue is converted, by means of dilute hydrochloric acid, into the hydrochloride, which is recrystallized from an ethanol/ether mixture. 10.0 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl β-dimethylaminoethyl ether bis-hydrochloride, of melting point 213°-214° C., are obtained.

Provenance & Evidence