1-[2-(3-methylbutoxy)phenethyl]pyrrolidinium chloride

Somagest,Riom,France,1972

There is heated under reflux with stirring for 10 hours: 117 g of (2-phenyl-2-isoamyloxy)ethyl bromide, 61.5g of pyrrolidine and 250 ml of toluene.
After filtration of the pyrrolidine hydrobromide, the toluene is removed under reduced pressure. The residue is then taken up with 4 N HCl. The aqueous solution is washed with ether. It is made alkaline by a solution of 50% NaOH. It is extracted with ether. The ethereal phase is dried over anhydrous sodium sulfate, and rectified under reduced pressure after removing the solvent. There is thus obtained 90 g of a colorless oil with an amine odor.
The hydrochloride is prepared in the usual manner by dissolving the amine in anhydrous ether and adding to it the requisite amount of dry gaseous hydrochloric acid, dissolved in absolute alcohol. There is obtained a white crystalline powder melting at 150°C, very soluble in water and alcohol, very slightly soluble in ether and ethyl acetate.
The starting material above is prepared by reacting styrene with isoamyl alcohol and then reacting that product with t-butyl hypobromite.

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