1-(4-(Benzyloxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one → 6-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)piperidin-2-one

HRID 594368Notes

Reaction equation

HRID 594368 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH:19]([C:20]3[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[O:28][CH3:29])[CH2:18][CH2:17][CH2:16][C:15]2=[O:30])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO>[CH3:29][O:28][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:20]=1[CH:19]1[N:14]([CH2:13][C:12]2[CH:31]=[CH:32][C:9]([OH:8])=[CH:10][CH:11]=2)[C:15](=[O:30])[CH2:16][CH2:17][CH2:18]1

Participants

3

Reactant 1

HCID 690813511-(4-(Benzyloxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

Product 1

HCID 690817446-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-(benzyloxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one (74 mg; 0.17 mmol), and 10% Pd(C) (35 mg) in anh. EtOH (3 ml) was stirred at rt, under hydrogen atmosphere (1 atm), for 15 h. Filtration over a pad of celite, concentration to dryness under reduced pressure, and additional drying under HV afforded 6-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)piperidin-2-one as a yellow oil. LC-MS (conditions E): tR=0.62 min.; [M+H]+: 342.20 g/mol.

Workup

  1. filtrationFiltration
  2. concentrationover a pad of celite, concentration to dryness under reduced pressure
  3. customadditional drying under HV

Sources & evidence

ORD record
ord-22c71af979344fba8eeeb2bf0df19e3d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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