Hydrochloric Acid → 3-(3-Methoxy-phenyl)-piperidine-3-ol

HRID 1712022Notes

Reaction equation

HRID 1712022 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)([OH:14])[CH2:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136950931-Benzyl-3-(3-methoxyphenyl)piperidin-3-ol

Product 1

HCID 116516763-(3-Methoxy-phenyl)-piperidine-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

32.41 g of 1-benzyl-3-(3-methoxy-phenyl)-piperidine-3-ol were dissolved in methanol and adjusted to pH 6 with 12.4 g of 32% HCl solution. 3.3 g Pd/C 10% (in cooled methanol) were added under a nitrogen atmosphere. The mixture was hydrogenated overnight at 5 bar H2 pressure. The catalyst was then removed via a filter earth and the filtrate was concentrated by evaporation. The oily residue was taken up in H2O, made alkaline with NaOH, and extracted three times with diethyl ether. The combined organic phases were dried over MgSO4 and concentrated by evaporation. Yield 20.92 g

Workup

  1. customThe catalyst was then removed via a filter earth
  2. concentrationthe filtrate was concentrated by evaporation
  3. extractionextracted three times with diethyl ether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-479fcb89482049febd8619fb41a3a6ea
Source dataset
uspto-grants-2010_09
Patent number
US07790898B2

Reaction notes

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