Hydrochloric Acid → 4-Benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidin-4-ol hydrochloride

HRID 1419892Notes

Reaction equation

HRID 1419892 reaction equation
[CH2:1]([C:8]1([OH:31])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:32]>CO.C(OCC)(=O)C.[Pd]>[ClH:32].[CH2:1]([C:8]1([OH:31])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 700459094-Benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidin-4-ol

Product 1

HCID 232944494-Benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidin-4-ol hydrochlorideYield 72%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

4-Benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidin-4-ol (1.35 g, 3.2 mmol) was dissolved in a mixture of MeOH (75 ml) and ethyl acetate (75 ml) and hydrogenated in the presence of Pd on C at room temperature and atmospheric pressure. After filtration and evaporation of the solvent, the residue was dissolved in ethanol (2 mnl) and ethyl acetate (10 ml). 1.1 equivalent of ethanolic HCl were added to give 4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidin-4-ol hydrochloride (0.85 g, 72%) as colorless solid, m.p. 161°-163° C. and MS: m/e=328.3 (M+H+).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethanol (2 mnl)

Sources & evidence

ORD record
ord-63c2fc9015a34f9394b7b010ffbb963a
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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