Dimethyl Sulfoxide → 1-Phenethylamine

HRID 611951Notes

Reaction equation

HRID 611951 reaction equation
[OH-].[K+].[C:3]1([C@H:9]([NH2:11])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(C)=O>O>[C:3]1([CH:9]([NH2:11])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 74081-Phenethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Solid, powdered potassium hydroxide (4.6 mg, 8.2×10-5 mol) and (R)-1-phenylethylamine (98% ee) (1.00 g, 8.25×10-3 mol) are mixed with dimethyl sulfoxide (5 ml, 0.07 mol), and the mixture is heated to 80°C. and kept at this temperature for 16 h. The mixture is then cooled and diluted with water (5 ml), and the amine is extracted into ether (2×10 ml). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated to give 0.85 g (85%) of substantially racemic 1-phenylethylamine; purity >96% by 1HNMR, ratio (S):(R) recovered by HPLC with chiral column as 1:1.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionthe amine is extracted into ether (2×10 ml)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dec02670c92c44ac9ed7d902059ce4f7
Source dataset
uspto-grants-1999_12
Patent number
US06002045

Reaction notes

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