Ethanol → HCID 16334829, compound

HRID 841878Notes

Reaction equation

HRID 841878 reaction equation
C([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].C([OH:20])C>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:12]([OH:15])(=[O:20])[CH3:13].[NH:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 702EthanolHCID 2397261-benzyl-1,4-diazepan-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 16334829HCID 16334829, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

1-Benzylhexahydro-(5H)-1,4-diazepine-5-one (1.5 g, 7.34 mmol) was dissolved in 12 mL of ethanol and 6 mL of acetic acid. After addition of 150 mg of 20% palladium hydroxide on carbon, the mixture was shaken under 40 psi of hydrogen for 4 h. The resulting mixture was centrifuged and the supernatant was filtered through a 0.45 micron membrane filter. The catalyst was washed with ethanol (3×10 mL), and the combined filtrate was concentrated in vacuo to give a yellow oil which began to crystallize. Swirling with 2 mL of methanol and 1 mL of ethyl acetate facilitated the crystallization, and evaporation of the solvent in vacuo gave 1.23 g (96%) of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt as light yellow crystals.

Workup

  1. filtrationthe supernatant was filtered through a 0.45 micron membrane
  2. filtrationfilter
  3. washThe catalyst was washed with ethanol (3×10 mL)
  4. concentrationthe combined filtrate was concentrated in vacuo
  5. customto give a yellow oil which
  6. customto crystallize
  7. customthe crystallization, and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-06268393d6ed4959847f49734ed1d272
Source dataset
uspto-grants-2002_04
Patent number
US06372733B1

Reaction notes

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