Isopropanol → HCID 20306007, compound

HRID 1732345Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:13]1O[CH:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([OH:25])(C)C>O1CCCC1.CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:25])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

N-Acetyl-4-hydroxypiperidine (5.0 g.) in tetrahydrofuran (THF) (50 ml.) was added to a stirred suspension of sodium hydride (1.84 g., 50% dispersion in mineral oil) in tetrahydrofuran (THF) (25 ml.) under an atmosphere of nitrogen. When effervescence had ceased, styrene oxide (4.6 g.) in THF (25 ml.) was added, then the reaction mixture was diluted with dimethylformamide (DMF) (25 ml.) and stirred at 60° C. for 18 hours. After addition of isopropanol to the cooled solution, the solvent was removed in vacuo, the residue treated with water, adjusted to pH 4 with 2 N hydrochloric acid, and extracted with chloroform. The chloroform extract was dried (Na2SO4) and the solvent evaporated in vacuo to give N-acetyl-4(2-hydroxyphenethyloxy)piperidine. This product in ethanol (50 ml.) and 5 N sodium hydroxide solution (100 ml.) was heated under reflux for 3 hours. The solvent was then removed in vacuo, the residue taken up in water, extracted with chloroform, dried and the solvent evaporated in vacuo. The product in chloroform was converted to the hydrochloride salt by treatment with ethereal hydrogen chloride and evaporation of the solvent.

Workup

customthe solvent was removed in vacuo
additionthe residue treated with water
extractionextracted with chloroform
extractionThe chloroform extract
dry with materialwas dried (Na2SO4)
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-16a804fc0243466da8b42e012b873565
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237138

Reaction notes

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