HCID 11367272, compound → HCID 64506015, compound

HRID 1464913Notes

Reaction equation

HRID 1464913 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]#[C:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8].[H][H]>O1CCCC1.[Ru]>[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][CH2:4][CH:5]1[CH2:11][CH2:10][CH2:9][CH:7]([NH2:8])[CH2:6]1

Participants

5

Reactant 2

HCID 11367272HCID 11367272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 64506015HCID 64506015, compound

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of Ru/C 5% is added to a solution consisting of 1.04 g (0.6 mol) of 3-(3,3-dimethylbut-1-yn-1-yl)aniline in 20 ml of tetrahydrofuran, and the mixture is hydrogenated with 100 bar of hydrogen at 120° C. for 40 hours. After cooling to room temperature, the catalyst is filtered off through kieselguhr and the product is concentrated under reduced pressure. This gives 0.9 g (81% of theory) of 3-(3,3-dimethylbutyl)cyclohexanamine as main component according to MSD-HPLC.

Workup

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

Sources & evidence

ORD record
ord-a0bf79a08e8148dca1eb60526a7f6ca1
Source dataset
uspto-grants-2015_04
Patent number
US08999956B2

Reaction notes

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