Oxygen isosteric derivatives of 3-(3-hydroxyphenyl)-Nn-propylpiperidine

…, M Leopoldo, V Tortorella, MD Lograno…

Index: Perrone, Roberto; Berardi, Francesco; Leopoldo, Marcello; Tortorella, Vincenzo; Lograno, Marcello D.; et al. Journal of Medicinal Chemistry, 1992 , vol. 35, # 16 p. 3045 - 3049

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Citation Number: 16

Abstract

Chemistry The compounds 4a-g, j, k and 5a, b are commercially available. Two different methods were used to obtain arylmorpholines loa-i, starting from corresponding arylketones 4a-i and by subsequent a-bromination to compound 5a-i, as shown in Scheme I. The first one involved carbonyl reduction by NaBH4 to the bromohydrins 6a-d and oxirane ring closure in alkaline medium. Epoxides 7a-d were reacted with Nn-propylamine to yield ...