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

HRID 1281906Notes

Reaction equation

C(OC([CH2:6][CH2:7][NH:8][CH:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH:10]([CH3:16])[C:11]([O:13]CC)=O)=O)C.CC(C)([O-])C.[K+].C(O)C>C1(C)C=CC=CC=1.O>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][CH:9]1[CH:10]([CH3:16])[C:11](=[O:13])[CH2:6][CH2:7][NH:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

customformed
distillationis distilled off
waitThen the mixture is left
temperatureto cool
temperaturerefluxed for 3 h
extractionthe aqueous phase is extracted three times with 400 mL of diethylether (ether)
dry with materialThe combined organic phases are dried over magnesium sulfate

Sources & evidence

ORD record: ord-89b4d555c6ea4a978bcbbc32f460cb38
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455538B1

Reaction notes

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