Hydrochloric Acid → 2-[3-(3-Hydroxyphenyl)-piperidino]ethanol hydrochloride

HRID 2108201Notes

Reaction equation

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

Participants

Conditions

Temperature: -30 °C

Procedure

Ethylenoxide (0.36 ml, 7.0 mmol) was added to a stirred solution of 3-(3-hydroxyphenyl)piperidine (1.0 g, 5.6 mmol) in methanol (150 ml), maintaining the temperature at -30° C., whereafter the reaction mixture was allowed to reach room temperature. (The reaction was followed by TLC). More ethylenoxide (0.5 ml, 9.8 mmol) was added in portions until the reaction was complete (two weeks). An excess of ethereal hydrogen chloride was added and the solvent was evaporated. The oily residue was passed through a silica column with 10% methanol in chloroform. After evaporation the hydrochloride was recrystallized from ethanol/ether to yield 0.6 g (41%) of 2-[3-(3-hydroxyphenyl)-piperidino]ethanol hydrochloride, m.p. 116.5°-120° C.

Workup

customto reach room temperature
custom(two weeks)
customthe solvent was evaporated
customAfter evaporation the hydrochloride
customwas recrystallized from ethanol/ether

Sources & evidence

ORD record: ord-437a9ef14ac14818ac1a8a0d919bd46e
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04937346

Reaction notes

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