Methyl iodide → 1-Acetyl-3-benzylidene-4-methylpiperazine-2,5-dione

HRID 1458550Notes

Reaction equation

HRID 1458550 reaction equation
[C:1]([N:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6](=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]1=[O:18])(=[O:3])[CH3:2].CI.[C:21]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:1]([N:4]1[CH2:9][C:8](=[O:10])[N:7]([CH3:21])[C:6](=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]1=[O:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 37596531-Acetyl-3-benzylidene-2,5-piperazinedione2×

Product 1

HCID 545742291-Acetyl-3-benzylidene-4-methylpiperazine-2,5-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Acetyl-3-benzylidene-2,5-piperazinedione (compound 18 prepared in Reference Example 2) was N-methylated by treatment with methyl iodide (2.0 equivalents) in the presence of Na2CO3 (1.0 equivalents) in DMF at room temperature for 24 hours. The solvent was removed and the residue purified by flash chromatography. The product 1-acetyl-3-benzylidene-4-methyl-2,5-piperazinedione, obtained in 45% yield, was treated with 4-methoxybenzaldehyde (1.0-1.1 equivalents) in the presence of Cs2CO3 in DMF at 80° C. for 206 hours to give compound 121, which is (3Z,6Z)-6-benzylidene-3-(4-methoxybenzylidene)-1-methyl-2,5-piperazinedione, in 35% yield.

Workup

  1. customThe solvent was removed
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-8edeee7c007747bd80d8569064dbe38a
Source dataset
uspto-grants-1998_12
Patent number
US05852018

Reaction notes

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