Ethylene Oxide → Ethyl 1-(2-hydroxyethyl)-4-phenylpiperidine-4-carboxylate

HRID 1833371Notes

Reaction equation

[C:1]1([C:7]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)[CH2:20][C:21](=[O:23])C.C1OC1>C(O)C>[OH:23][CH2:21][CH2:20][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 9.9 parts of ethyl 4-phenyl-4-piperidinecarboxylate, 41.8 parts of 4-methyl-2-pentanone, 4.3 parts of ethylene oxide and 79.2 parts of ethanol is heated in a sealed citric bottle at about 60° C for 7 days. The resulting solution is cooled, the solvent is evaporated under reduced pressure and the residual material is partitioned between diluted NaOH and ether. The ether layer is then separated and extracted with diluted HCl. The acid layer is then made alkaline with aqueous sodium hydroxide and the resulting mixture is extracted with ether. The ether layer is dried over sodium sulfate and potassium carbonate and evaporated in vacuum. The residue is crystallized from ether-n-pentane to give ethyl 1-(2-hydroxyethyl)-4-phenyl-4-piperidinecarboxylate, melting at about 91.5°-93° C.

Workup

temperatureThe resulting solution is cooled
customthe solvent is evaporated under reduced pressure
customthe residual material is partitioned between diluted NaOH and ether
customThe ether layer is then separated
extractionextracted with diluted HCl
extractionthe resulting mixture is extracted with ether
dry with materialThe ether layer is dried over sodium sulfate and potassium carbonate
customevaporated in vacuum
customThe residue is crystallized from ether-n-pentane

Sources & evidence

ORD record: ord-b360bb82430c4fa9b93e45c9d5d136a4
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066654

Reaction notes

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