ChemInform Abstract: An Approach to 1-Alkyl-3-phenylpiperidine Derivatives Containing 2,5- Functionalized Groups: 1-Methyl-2-(4-chlorophenylthiomethyl)-5-( methoxycarbonyl)piperidine

Autor:	Christos G. Gourdoupis, Ioannis K. Stamos, Heleni K. Kotzamani
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Annulation Ketone Methylamine Carboxylic acid chemistry.chemical_element General Medicine Catalysis Rhodium chemistry.chemical_compound chemistry Polymer chemistry Piperidine Alkyl
Zdroj:	ChemInform. 26
ISSN:	0931-7597
DOI:	10.1002/chin.199508191
Popis:	Compound 6 was synthesized by regiospecific addition of 4-chlorothiophenol to diazoketone 5 in the presence of a rhodium (II) acetate catalyst. An annelation process pressumably proceeded via initial attack of methylamine on the bromoacrylic ester to give the methyl α-(methylamino)methylacrylate. Reaction with ketone 6 then leads to intermediate acrylicenamine formation followed by cyclization to the unsaturated piperidine ring. Reduction of this cyclic with sodiumcyanoborohydride in the presence of carboxylic acid produced the piperidine derivative 1-methyl-2-(4-chlorophenylthiomethyl)-5-methoxycarbonyl-piperidine.
Databáze:	OpenAIRE
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