Tyramine → 4-(2-Aminoethyl)cyclohexan-1-ol

HRID 850464Notes

Reaction equation

HRID 850464 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Pt](=O)=O>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][NH2:10])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 5610TyramineHCID 178418361HCID 178418361, compound

Product 1

HCID 177736214-(2-Aminoethyl)cyclohexan-1-olYield 125.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-Hydroxyphenyl)ethylamine (1.37 g, 10.0 mmol, 1.0 eq ) was dissolved in acetic acid (10 ml), and platinum dioxide catalyst (137 mg) was added. The mixture was stirred at 3 kgf/cm2 in a stream of hydrogen at 70° C. for 5 hours. The reaction mixture was filtered through Celite and the catalyst was washed with toluene. The filtrate was concentrated under reduced pressure to give 2-(4-hydroxycylohexyl)ethylamine (1.8 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe catalyst was washed with toluene
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6612bf25ee44d98b98a7cc2f44e72a4
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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