1,4-Cyclohexadiene → HCID 21955233, compound

HRID 2213044Notes

Reaction equation

HRID 2213044 reaction equation
C1CC=CCC=1.[CH3:7][N:8]1[C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][C:15]2=[O:30])=[N:11][CH:10]=[N:9]1>[Pd].C(O)C>[CH3:7][N:8]1[C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]2=[O:30])=[N:11][CH:10]=[N:9]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 21955331HCID 21955331, compound

Product 1

HCID 21955233HCID 21955233, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of palladium on carbon (10%, 1.7 g) and 1,4-cyclohexadiene (4.1 g, 51 mmol) in ethanol (10 mL) was added to a solution of phenylmethyl 4-[(1-methyl-1H-1,2,4-triazol-5-yl)methyl]-3-oxo-1-piperazinecarboxylate (Description 140, 1.7 g, 5.2 mmol) in ethanol (40 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was filtered through Celite™ and the solvent was evaporated under reduced pressure, The residue was recrystallized from propan-2-ol to give the title compound (500 mg, 49%). m/z (ES+) 196 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was recrystallized from propan-2-ol

Sources & evidence

ORD record
ord-bc9458cbd9294826b623b1312b67b3d0
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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