An approach to 1-alkyl-3-phenylpiperidine derivatives containing 2,5-functionalized groups: 1-methyl-2-(4-chlorophenylthiomethyl)-5-(methoxycarbonyl)- piperidine.

Add time:09/03/2019    Source:sciencedirect.com

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.

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