2-(1,3-Dimethylbutyl)aniline → 2-(1,3-Dimethylbutyl)cyclohexanamine

HRID 2068496Notes

Reaction equation

HRID 2068496 reaction equation
[CH3:1][CH:2]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])[CH2:3][CH:4]([CH3:6])[CH3:5].[H][H]>O1CCCC1.[Ru]>[CH3:1][CH:2]([CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:8]1[NH2:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 115284412-(1,3-Dimethylbutyl)anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 167270572-(1,3-Dimethylbutyl)cyclohexanamine

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5 g of Ru/C (5%) are added to a solution comprising 20.0 g (0.113 mol) of 2-(1,3-dimethylbutyl)aniline in 300 ml of tetrahydrofuran, and the mixture is hydrogenatcd with 100 bar of hydrogen at 120° C. for 24 hours. After cooling to room temperature, the catalyst is filtered off through Celite 545 and the product is concentrated under reduced pressure. This gives 19.1 g (92.4% of theory) of 2-(1,3-dimethylbutyl)cyclohexanamine having a purity of 100% according to HPLC and a log P (pH 2.3) of 4.07.

Workup

  1. filtrationthe catalyst is filtered off through Celite 545
  2. concentrationthe product is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ddc062e39f064105ada5e7930eb3a9ab
Source dataset
uspto-grants-2012_10
Patent number
US08299047B2

Reaction notes

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