Hydrochloric Acid → Indecainide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

The pH of a cold (10° C.) solution of 12.0 ml of isopropylamine in 500 ml of acetonitrile was adjusted to 8.0 by addition of gaseous hydrogen chloride. While the reaction mixture was stirred there were added sequentially 2.0 g of sodium cyanoborohydride and 5.4 g of 6'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-one (the cyclic carbinol and its tautomer prepared as described in Examples 1 and 2). The reaction mixture was heated at reflux for six hours, cooled to 25° C. and then diluted by addition of 100 ml of 1N hydrochloric acid. The organic solvent was removed by evaporation under reduced pressure. The aqueous solution was washed several times with dichloromethane, made alkaline by addition of ammonium hydroxide, and the product was extracted into fresh dichloromethane. The organic extracts were combined, washed with water, dried and concentrated to dryness to give 70% yield of 9-carbamoyl-9-(3-isopropylaminopropyl)fluorene, the identity of which was confirmed by thin layer chromatographic comparison with an authenic sample (silica gel, ethyl acetate:methanol, 80:20 v/v).

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