Triethylamine → Eproxindine

Participants

Reaction Steps

The resulting ethereal solution of N-phenyl-3-methoxyindole-2-carboxylic acid chloride is added dropwise to a solution of 579 g of 1-amino-2-hydroxy-3-diethylaminopropane and 40 g of triethylamine in 70 ml of methylene chloride, whilst cooling with ice. The reaction mixture is stirred at room temperature for 1 hour and then extracted with dilute hydrochloric acid. The hydrochloric acid extract is rendered alkaline by addition of sodium hydroxide solution and is extracted with ether. The ether solution is washed with water, dried over sodium sulphate and evaporated. 110 g of 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-phenylindole remain as an oily base. This base is dissolved in isopropanol and converted into its hydrochloride. Yield: 110 g of the hydrochloride=60.6%, melting point: 148°-150° C.

Provenance & Evidence