Cyclohexene → HCID 22393276, compound

HRID 480022Notes

Reaction equation

HRID 480022 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1.C1CCCCC=1>[Pd].C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 3573319HCID 3573319, compound

Product 1

HCID 22393276HCID 22393276, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-{N-[3-(imidazol-1-yl)propyl]carbamoyl}nitrobenzene (Method 41; 2.0 g, 7.30 mmol), 10% palladium on carbon (100 mg) cyclohexene (40 ml) and ethanol (80 ml) was heated under reflux under an atmosphere of nitrogen for 4 hours. Two further portions of cyclohexene (40 ml) were added and heating was continued for 1 hour after each addition. The mixture was left to cool and the catalyst was removed by filtration. The filtrate was concentrated by evaporation and the residue was recrystallized from a mixture of ethanol and ether to give the product (1.2 g, 67%). NMR: 1.9-2.0 (m, 2H), 3.1-3.2 (m, 2H), 4.0 (t, 2H), 5.6 (br s 2H), 6.55 (d, 2H), 6.85 (s, 1H), 7.2 (s, 1H), 7.55 (d, 2H), 7.65 (s, 1H), 8.0 (br t, H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an atmosphere of nitrogen for 4 hours
  3. temperatureheating
  4. additionafter each addition
  5. waitThe mixture was left
  6. temperatureto cool
  7. customthe catalyst was removed by filtration
  8. concentrationThe filtrate was concentrated by evaporation
  9. customthe residue was recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-e59abd7e1d484ae280c6174c38db85af
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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