Toluene → N-Ethyl-2-(3-chloro-2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

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Reaction Steps

30 ml of thionyl chloride is added to 17.0 g (0.078 mol) of 3-chloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 10.0 g (0.078 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of methyl ethyl ketone. After stirring for 30 minutes at room temperature 150 ml of ether is added. The obtained precipitate is filtered off, washed with ether and recrystallized twice from ethanol - isopropyl ether. Yield: 21.3 g, m.p. 175°-77° C. (first recrystallization). m.p. 179°-80° C. (second recrystallization).

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