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  • 标题:Studies on the Syntheses of Ring Substituted p-Alkylephedrines and p-Alkylnorephedrines
  • 本地全文:下载
  • 作者:Takeo Ueda ; Kiyoshi Takahashi ; Masako Muraoka
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:1956
  • 卷号:4
  • 期号:3
  • 页码:182-188
  • DOI:10.1248/cpb1953.4.182
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:Alkylbenzenes were condensed with propionic anhydride in the presence of aluminum chloride into p-alkyl propiophenones, which were converted into p-alkyl-α-isonitrosopropiophenones by treatment with butyl nitrite. These isonitrosoketones were first reduced into aminoketones in dehyd. ethanol containing hydrogen chloride in the presence of palladium-carbon catalyst, and the p-alkyl-α-aminopropiophenone hydrochlorides were converted into amino alcohols in water by the aid of the same kind of catalyst. α-(p-Alkylphenyl)-β-aminopropanols, or p-alkyl-norephedrines, thereby obtained are probably a mixture of compounds of regular and pseudo forms. In order to obtain each of them separately from the mixture, the elaborate method of Taguchi et al. was applied in a modified form. By these mothods, p-methyl-, p-ethyl-, p-propyl-, p-butyl-, p-amyl-, p-hexyl-, p-heptyl-, p-otyl-, p-decyl-, and p-dodecyl-ephedrines and the corresponding norephedrines were obtained. In addition, these ring-substituted ephedrines and norephedrines were divided into the regular- and pseudo-series.
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