[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]=1Ethylenoxide (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.
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