4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3-(1-methylethyl)-2-piperazinone → 3-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone

HRID 1972561Notes

Reaction equation

HRID 1972561 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH:23]1[CH:29]([CH3:31])[CH3:30])C1C=CC=CC=1>C(O)C.[Pd]>[CH3:31][CH:29]([CH:23]1[N:22]([CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH2:27][CH2:26][NH:25][C:24]1=[O:28])[CH3:30]

Participants

4

Reactant 1

HCID 665833974-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3-(1-methylethyl)-2-piperazinone

Product 1

HCID 665825553-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3-(1-methylethyl)-2-piperazinone (0.414 g, 0.984 mmol) in ethanol (4.92 mL) was placed under an atmosphere of N2 and charged with 10% palladium on carbon (10% wt. (dry basis) on activated carbon, wet, Degussa type (0.314 g, 0.295 mmol, Sigma-Aldrich, St. Louis, Mo.)). The mixture was purged with hydrogen gas and stirred at room temperature under a hydrogen atmosphere (1 atm) for 72 h. The solids were then removed by filtering through a pad of Celite® (diatomaceous earth), rinsing with EtOH, the filtrate was concentrated, and the product was carried forward without further purification (238 mg).

Workup

  1. customThe mixture was purged with hydrogen gas
  2. customThe solids were then removed
  3. filtrationby filtering through a pad of Celite® (diatomaceous earth)
  4. washrinsing with EtOH
  5. concentrationthe filtrate was concentrated
  6. customthe product was carried forward without further purification (238 mg)

Sources & evidence

ORD record
ord-07c64216c1224359845116501fab3b68
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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