Hydrochloric Acid → 2-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)-1-ethanamine Hydrochloride

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Reaction Steps

To a suspension of 6.9 parts by weight of 5-chloro-2-phenylbenzo[b]thiophene-3-acetonitrile in a solution of 11.6 parts by weight of cobaltous chloride hexahydrate in 300 parts by volume of methanol-benzene (5:1) is added, slowly, 9.2 parts by weight of sodium borohydride at 0° C. After the addition is completed, the mixture is allowed to warm to room temperature and then stirred for 19 hours. To the solution is now added 100 parts by volume of 3N hydrochloric acid. The solution is then stirred an additional 2 hours. The reaction mixture is partitioned between water and ether. The aqueous layer is separated, basified with concentrated ammonium hydroxide and extracted (3xs) with ether. The organic fractions are combined, washed with brine, dried over magnesium sulfate and concentrated to afford crude 5-chloro-2-phenylbenzo[b]thiophene-3-ethaneamine as a yellow oil. This oil is dissolved in 15 parts by volume of isopropanol; to this solution is then added 8.0 parts by volume of isopropanolic/HCl. A solid precipitates out; 30 parts by volume of ethyl ether is now added and the mixture is stirred overnight. Removal by vacuum filtration of the resulting white solid material affords 5-chloro-2-phenylbenzo[b]thiophene-3-ethanamine hydrochloride, melting dec > 250° C. This compound is represented by the following structural formula ##STR19##

Provenance & Evidence