3,5-Dimethylaniline → 3,5-diMethyl-cyclohexylaMine

HRID 1463835Notes

Reaction equation

HRID 1463835 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5]>[Ru]>[CH3:1][CH:2]1[CH2:8][CH:7]([CH3:9])[CH2:6][CH:4]([NH2:5])[CH2:3]1

Participants

3

Reactant 1

HCID 79493,5-Dimethylaniline

Product 1

HCID 146753743,5-diMethyl-cyclohexylaMine

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Procedure

N-cis, cis-3,5-Dimethylcyclohexyl-N-cyclopentyl amine is synthesized as shown in Scheme M. 3,5-Dimethylcyclohexyl amine is synthesized by catalytic hydrogenation of 3,5-dimethyl aniline for 7 to 24 hours. A suitable catalyst is 5% ruthenium on carbon. Hydrogenation pressure may change from 500 to 1500 psi and temperatures may range from 80° to 150°. N-cis cis-3,5-Dimethylcyclohexyl-N-cyclopentyl amine is formed by reductive amination of cyclpentanone with 3,5-dimethylcyclohexyl amine. The reductive amination may be carried out by hydrogenation using palladium on carbon as catalyst at pressures ranging from 15 to 90 psi. The temperature may range from room temperature to 50°. The reaction time is from 7 to 48 hours.

Workup

  1. customN-cis, cis-3,5-Dimethylcyclohexyl-N-cyclopentyl amine is synthesized
  2. custommay range from 80° to 150°

Sources & evidence

ORD record
ord-5c3fca26dacd4245867dc83c1a5f047a
Source dataset
uspto-grants-1994_04
Patent number
US05302601

Reaction notes

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