4-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine → 4-(4-(Dimethylamino)cyclohexyl)-2-isopropoxy-5-methylaniline

HRID 386795Notes

Reaction equation

HRID 386795 reaction equation
[CH:1]([O:4][C:5]1[C:6]([N+:21]([O-])=O)=[CH:7][C:8]([CH3:20])=[C:9]([C:11]2[CH2:16][CH2:15][CH:14]([N:17]([CH3:19])[CH3:18])[CH2:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2]>CO.[Pd]>[CH3:19][N:17]([CH3:18])[CH:14]1[CH2:13][CH2:12][CH:11]([C:9]2[C:8]([CH3:20])=[CH:7][C:6]([NH2:21])=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:10]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 597644704-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine

Product 1

HCID 597645904-(4-(Dimethylamino)cyclohexyl)-2-isopropoxy-5-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine (0.1 mmol) in 10 mL of MeOH, is added Pd/C (5 mg) under argon. The suspension is stirred under 1 atm. H2 for 6 hours. After filtering, solvent is removed and 4-(4-(dimethylamino)cyclohexyl)-2-isopropoxy-5-methylaniline is obtained. MS (ES+): 291.24 (M+1)+.

Workup

  1. filtrationAfter filtering
  2. customsolvent is removed

Sources & evidence

ORD record
ord-80db498f6d73483e9c30036d913666b2
Source dataset
uspto-grants-2013_02
Patent number
US08372858B2

Reaction notes

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