Diethylamine → 2H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

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Reaction Steps

A solution of 0.84 g. of 5-chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-3-phenylisoindole-1-carboxylic acid ethyl ester in 5 ml. of dimethylsulfoxide is treated with 5 ml. of diethylamine and boiled at reflux for 17 hours under exclusion of light. The excess diethylamine is then evaporated under reduced pressure and the resulting solution poured into 50 ml. of ice-water. After the addition of 3 g. of sodium chloride, the separated, thick oil is extracted with methylene chloride. The organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated to dryness under reduced pressure. The oily residue is dissolved in 15 ml. of acetone, treated with 10 ml. of 0.5-N hydrochloric acid and the mixture is thoroughly shaken. After cooling in an ice-bath, the crystallized hydrochloride is isolated and purified in a manner analogous to that described in Example 1, and there is obtained 5-chloro-2-[2-(diethylamino)-ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 248°-250° C. (decomposition).

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