HCID 19754690, compound → 2-(3,3,5,5-Tetramethylcyclohexyl)phenylamine

HRID 604840Notes

Reaction equation

HRID 604840 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:3]1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1([CH3:17])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])[CH2:3]1

Participants

5

Reactant 2

HCID 19754690HCID 19754690, compoundHCID 178418361HCID 178418361, compound6×

Product 1

HCID 119922852-(3,3,5,5-Tetramethylcyclohexyl)phenylamineYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 100 mL autoclave, 10% palladium on carbon (water content 50%, 1.2 g) was added to a solution of 2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine (4.00 g, 17.4 mmol) in ethanol (40 mL), followed by stirring at room temperature, 5 kgf/cm2 of hydrogen pressure for 5.5 hours. Then the reaction mixture was stirred at room temperature, 10 kgf/cm2 of hydrogen pressure for 3 hours, introduction of hydrogen was stopped, and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was stirred at room temperature, 10 kgf/cm2 of hydrogen pressure for 9.5 hours, introduction of hydrogen was stopped, and the reaction mixture was stirred at room temperature for 13 hours. The reaction mixture was stirred at room temperature, 10 kgf/cm2 of hydrogen pressure for 7.5 hours, and the reaction mixture was stirred at room temperature. The pressure was brought to atmospheric pressure, and the reaction mixture was filtered through Celite, and concentrated to give 3.90 g of the title compound as a brown oil.

Workup

  1. stirringThen the reaction mixture was stirred at room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 15 hours
  3. stirringThe reaction mixture was stirred at room temperature
  4. stirringthe reaction mixture was stirred at room temperature for 13 hours
  5. stirringThe reaction mixture was stirred at room temperature
  6. stirringthe reaction mixture was stirred at room temperature
  7. filtrationthe reaction mixture was filtered through Celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-487eecf69936401c8dc450f4424ac67a
Source dataset
uspto-grants-2011_03
Patent number
US07910734B2

Reaction notes

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