Benzenamine, N-1-cyclohexen-1-yl- → HCID 54276649, compound

HRID 1440223Notes

Reaction equation

HRID 1440223 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12]C=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:14][CH2:15]O.[CH3:17]C(O)=O>[Pd]>[CH3:17][C:15]1([CH3:14])[CH2:12][CH2:13][CH:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 12210654Benzenamine, N-1-cyclohexen-1-yl-HCID 18476134Acetic acid ethanol

Product 1

HCID 54276649HCID 54276649, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a Parr hydrogenation flask, cyclohexenylaniline (46.4 g, 0.247 mol) is dissolved in 30 mL of 3:1 EtOH/AcOH and 10% Pd on carbon (0.5 g) is added. The reaction is shaken under H2 (60 psi) overnight. The mixture is filtered through a pad of celite and concentrated under vacuum. The crude product is dissolved with CH2Cl2 and neutralized with saturated aqueous bicarbonate. The organic layer is washed with water, dried over MgSO4 and concentrated to give a the 4,4-Dimethylcyclohexyl aniline as a light yellow oil (42.2 g, 90%).

Workup

  1. filtrationThe mixture is filtered through a pad of celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe crude product is dissolved with CH2Cl2 and neutralized with saturated aqueous bicarbonate
  4. washThe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-21b5d48361424d0bab925af533b52493
Source dataset
uspto-grants-1996_03
Patent number
US05498624

Reaction notes

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