Ethanol → 2-(2-Methoxyphenyl)methyl-3-methyl-4-piperidone

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Reaction Conditions

Reaction Steps

210 g (0.6 mol) of ethyl 3-(2-ethoxycarbonylethyl)-amino-4-(2-methoxyphenyl)-2-methylbutanoate 14 are dissolved in 3 1 toluene and first about 100 mL of a solvent/water mixture are entrained. The mixture is cooled to about 70° C., combined with 80 g (0.7 mol) of potassium tert-butoxide and heated for 30 minutes to 105° C., while the ethanol formed is distilled off. Then the mixture is left to cool and the solvent is eliminated in vacuo. The residue is combined with 400 mL of ethanol and 200 mL of 40% sodium hydroxide solution and refluxed for 3 h. The alcohol is eliminated in vacuo and the aqueous phase is extracted three times with 400 mL of diethylether (ether). The combined organic phases are dried over magnesium sulfate, and the solvent is eliminated in vacuo. Yield 109 g (78%) oil.

Provenance & Evidence