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

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Reaction Steps

A solution of 0.84 g. of 2-[3-(N-ethylacetamido)propyl]-5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester in 5 ml. of tetrahydrofuran is added dropwise under argon at room temperature to 3 ml. of a 1-M solution of borane in tetrahydrofuran. Subsequently, the mixture is heated at reflux for 4 hours, then treated at 15°-20° C. with 0.8 ml. of 6-N hydrochloric acid and the tetrahydrofuran is removed by distillation at atmospheric pressure. The residue is partitioned between 3 ml. of water and 5 ml. of ether and cooled in an ice-bath. The crystallized hydrochloride is isolated and purified in a manner analogous to that described in Example 5, and there is obtained 5-chloro-2-[3-(diethylamino)-propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride having a melting point of 203°-206° C. (decomposition).

Provenance & Evidence