(-)-N-benzyl-3-(3-methoxyphenyl)piperidine hydrochloride → 3-(3-Methoxyphenyl)piperidine hydrochloride

HRID 2108198Notes

Reaction equation

HRID 2108198 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[ClH:1].[CH3:22][O:21][C:17]1[CH:16]=[C:15]([CH:11]2[CH2:12][CH2:13][CH2:14][NH:9][CH2:10]2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 23045634(-)-N-benzyl-3-(3-methoxyphenyl)piperidine hydrochloride

Product 1

HCID 199872553-(3-Methoxyphenyl)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(-)-N-benzyl-3-(3-methoxyphenyl)piperidine hydrochloride (3.8 g, 0.0120 mol) was dissolved in ethanol (80 ml), 10% Pd/C was added and the mixture was hydrogenated at room temperature and atmospheric pressure (28 h). The catalyst was removed (Celite) by filtration, the solvent was evaporated off and the crystalline residue was recrystallized from methanol-ether giving the desired (+)-3-(3-methoxyphenyl)-piperidine hydrochloride (2.54 g, 30% total yield of the maximal theoretical) m.p. 175.5°-177° C.; [α]22D+10.1° (C 2.1, CH3OH).

Workup

  1. customwas hydrogenated at room temperature
  2. customatmospheric pressure (28 h)
  3. customThe catalyst was removed (Celite)
  4. filtrationby filtration
  5. customthe solvent was evaporated off
  6. customthe crystalline residue was recrystallized from methanol-ether giving the desired (+)-3-(3-methoxyphenyl)-piperidine hydrochloride (2.54 g, 30% total yield of the maximal theoretical) m.p. 175.5°-177° C.

Sources & evidence

ORD record
ord-83fd337615f346a491b3820685672f3d
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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