Reductive Amination of Ethynylpyridines with Sodium Cyanoborohydride

In order to investigate the structure-activity relationship of betahistine derivatives, a general synthesis of methylated 2-(2-methylaminoethyl) pyridines was developed based on the addition of methylamine hydrochloride to methylated 2-ethynylpyridines under reductive conditions. In addition, the sc...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 32; no. 12; pp. 4866 - 4872
Main Authors SAKAMOTO, TAKAO, NAGATA, HIDEO, KONDO, YOSHINORI, SATO, KAORI, YAMANAKA, HIROSHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 01.01.1984
Maruzen
Japan Science and Technology Agency
Subjects
2-(2-pyrideyl) ethylamine
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Chemical reduction
Addition reaction
Amination
Acetylenic compound
Nitrogen heterocycle
Six membered ring
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Summary:In order to investigate the structure-activity relationship of betahistine derivatives, a general synthesis of methylated 2-(2-methylaminoethyl) pyridines was developed based on the addition of methylamine hydrochloride to methylated 2-ethynylpyridines under reductive conditions. In addition, the scope and limitations of the reductive addition were briefly examined. For example, the reaction proceeded smoothly with p-nitrophenylacetylene, whereas phenylacetylene itself did not react with methylamine.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.32.4866