Hydrochloric Acid → HCID 70046883, compound

HRID 1419895Notes

Reaction equation

HRID 1419895 reaction equation
[CH2:1]([C:8]1([OH:32])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33]>CO.[Pd]>[ClH:33].[CH2:1]([C:8]1([OH:32])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70048093HCID 70048093, compound

Product 1

HCID 70046883HCID 70046883, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

4-Benzyl-1-[3-(4-benzyloxy-phenoxy)-propyl]-piperidin-4-ol (0.432 g, 1 mmol) was dissolved in MeOH (50 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 tetrahydrofuran (THF) (3 ml) and ether (10 ml). 1.1 equivalent of etheric HCl were added to give 4-benzyl-1-[3-(4-hydroxy-phenoxy)-propyl]-piperidin-4-ol hydrochloride (0.30 g, 88%) as colorless solid, m.p. 64° C. and MS: m/e=342.3 (M+H+).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. dissolutionthe residue was dissolved in tetrahydrofuran (THF) (3 ml)

Sources & evidence

ORD record
ord-4bdaf3829cf849fe8805aa61691f1853
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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