Potassium Carbonate → 1-[(4-Methoxyphenyl)methyl]piperidine-2,6-dione

HRID 596128Notes

Reaction equation

HRID 596128 reaction equation
[C:1]1(=[O:8])[NH:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CC(C)=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]2=[O:8])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 70726Glutarimide

Product 1

HCID 665869941-[(4-Methoxyphenyl)methyl]piperidine-2,6-dioneYield 87.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

Glutarimide (5 g, 44.2 mmol) was suspended in acetone (Volume: 100 mL) and then K2CO3 (12.22 g, 88 mmol), Bu4NI (3.27 g, 8.84 mmol) and 4-methoxybenzyl chloride (6.02 mL, 44.2 mmol) were added. The mixture was agitated at room temperature overnight and filtered through celite and then concentrated in vacuo and the residue purified by flash chromatography (0-50% EtOAc/heptane) to afford 8.99 g of the desired product as a colorless solid. LCMS (m/z): (MH+), 234.2, 0.66 min.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by flash chromatography (0-50% EtOAc/heptane)

Sources & evidence

ORD record
ord-8f6d07bcd2764ea79347d0906225801d
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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