HCID 53821861, compound → HCID 17964042, compound

HRID 1374973Notes

Reaction equation

HRID 1374973 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:13]=2)[C:5]1=[O:26])(=O)C>O1CCCC1.[C].[Pd]>[CH3:25][O:24][CH2:23][CH2:22][O:21][CH2:20][O:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[CH3:18])[CH2:11][CH:6]1[NH:7][C:8](=[O:10])[CH2:9][NH:4][C:5]1=[O:26]

Participants

4

Reactant 1

HCID 53821861HCID 53821861, compound

Product 1

HCID 17964042HCID 17964042, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetyl-3-[[3-[(2-methoxyethoxy)methoxy]-4-methylphenyl]methylene]-2,5-piperazinedione (2.0 g) in tetrahydrofuran (20 ml) was hydrogenated over 10% palladium-carbon (50% wet, 0.2 g) at room temperature under atmospheric pressure for 3 hours. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was dissolved into tetrahydrofuran (30 ml) and thereto was added hydrazine monohydride (1.5 ml). After being stirred for 1 hour at room temperature, the mixture was concentrated under reduced pressure. The residue was triturated with isopropyl alcohol and the resulting solid was collected by filtration to give 3-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-2,5-piperazinedione (1.75 g).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved into tetrahydrofuran (30 ml)
  5. additionwas added hydrazine monohydride (1.5 ml)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customThe residue was triturated with isopropyl alcohol
  8. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-a40ddee82bf6476d8e6cf11d1884f6a2
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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