Phenethylamine → 2-Cyclohexylethylamine

HRID 383135Notes

Reaction equation

HRID 383135 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH:3]1([CH2:2][CH2:1][NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 205092-Cyclohexylethylamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Phenethylamine (50 g) was dissolved in 1000 mL of glacial acetic acid in a pressure vessel, followed by addition of platinum oxide (15 g). After shaking under 4 atm of hydrogen for 48 h, the reaction was filtered and the acetic acid was removed under reduced pressure. The residue was taken up in water (1000 mL), basified with 5N NaOH, and washed with ether (5×250 mL). The ether extracts were washed with brine (250 mL), dried (MgSO4), filtered and concentrated to afford a light yellow oil which was purified by fractional distillation at atmospheric pressure (bp 185° C., 49.5 g, 94%).

Workup

  1. filtrationthe reaction was filtered
  2. customthe acetic acid was removed under reduced pressure
  3. washwashed with ether (5×250 mL)
  4. washThe ether extracts were washed with brine (250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a light yellow oil which
  9. distillationwas purified by fractional distillation at atmospheric pressure (bp 185° C., 49.5 g, 94%)

Sources & evidence

ORD record
ord-f1336f9969544fee814b0735bc037bbc
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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