In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 55, No. 7 ( 1990), p. 1828-1853
Abstract:
Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide ( I ) with phosphorus pentasulfide gave the thioamide VI . Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III . Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV . Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate ( XXII ) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX , a model compound in the synthesis of the cyclic analogue of fentanyl ( I ). Ethyl 4-anilino-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-3-carboxylate ( XXIX ) hydrochloride, obtained by reaction of ethyl 4-oxo-1-(2-phenylethyl)piperidine-3-carboxylate hydrochloride with aniline, was reduced with lithium aluminium hydride to 4-anilino-1-(2-phenylethyl)piperidine-3-methanol ( XXXI ). 1-Methyl- and 1-benzyl-4-piperidone were reacted with 4-cyclopropylphenylmagnesium bromide and the tertiary alcohols XXXVII and XXXVIII obtained were acylated with propionyl chloride to give the esters XXXIX and XL . The piperidine derivatives XLI, XLVI and XLVIII were prepared as potential neurotropic agents. Alkylation of 8-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine ( XLIX ) with 2-(2-chloroethyl)-1,3-dioxane and -1,3-dioxolane resulted in the 6,7-benzomorphan derivatives L and LI . Out of the compounds prepared, only the closest fentanyl analogues II, III , and VI showed very strong analgetic activity.
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc19901828
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
1990
