Sodium Acetate → (3Z)-3-{1-[(3-hydroxy-4-methoxybenzyl)amino]ethylidene}-4-phenylpiperidine-2,6-dione

HRID 2236623Notes

Reaction equation

HRID 2236623 reaction equation
O/[C:2](=[C:4]1\[C:5](=[O:17])[NH:6][C:7](=[O:16])[CH2:8][CH:9]\1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[CH3:3].[NH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:27][CH3:28])=[C:24]([OH:26])[CH:25]=1.C([O-])(=O)C.[Na+]>C(O)C>[OH:26][C:24]1[CH:25]=[C:20]([CH:21]=[CH:22][C:23]=1[O:27][CH3:28])[CH2:19][NH:18]/[C:2](=[C:4]1\[C:5](=[O:17])[NH:6][C:7](=[O:16])[CH2:8][CH:9]\1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[CH3:3]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 11329985-(Aminomethyl)-2-methoxyphenolHCID 68694730(3Z)-3-(1-hydroxyethylidene)-4-phenylpiperidine-2,6-dione

Product 1

HCID 59300292(3Z)-3-{1-[(3-hydroxy-4-methoxybenzyl)amino]ethylidene}-4-phenylpiperidine-2,6-dioneYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (3Z)-3-(1-hydroxyethylidene)-4-phenylpiperidine-2,6-dione (0.12 g, 0.52 mmol) and 5-(aminomethyl)-2-methoxyphenol (98 mg, 0.52 mmol) in absolute ethanol (5 mL) is added sodium acetate (0.75 mmol). The mixture is heated at reflux overnight and then allowed to cool to room temperature. The solvent is evaporated under reduced pressure and the residue is triturated with diethyl ether. The solid is collected, washed with diethyl ether, water, and methanol, and dried under vacuum to give (3Z)-3-{1-[(3-hydroxy-4-methoxybenzyl)amino]ethylidene}-4-phenylpiperidine-2,6-dione as a white powder (0.17 g, 88%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. customThe solvent is evaporated under reduced pressure
  4. customthe residue is triturated with diethyl ether
  5. customThe solid is collected
  6. washwashed with diethyl ether, water, and methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ffcd082288644aaeb3eaacea2ecc158f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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