HCID 3152239, compound → 1-Phenethylamine

HRID 1160673Notes

Reaction equation

HRID 1160673 reaction equation
[C:1]1([CH:7]([NH:9]CC#C)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]1([CH:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 3152239HCID 3152239, compound

Product 1

HCID 74081-PhenethylamineYield 77.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of N-(1-Phenylethyl)propargylamine (500 mg, 3.1 mmol) in THF (5 ml) was added to the LVT reagent prepared as described in Example 2.1 above, and the resulting mixture stirred for 2 hours at room temperature. The reaction mixture was diluted with hexane-ethyl acetate mixture (70:30) and filtered through celite. The filtrate washed with brine, dried (Na2SO4), and concentrated under vacuum. The crude product was purified using chromatography (SiO2) to yield 1-phenylethylamine (290 mg, 77%). The rotation (αD) of the de-protected 1-phenylethylamine was used to determine the ee of the products in Example 1.11.

Workup

  1. customprepared
  2. filtrationfiltered through celite
  3. washThe filtrate washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-2f1b95ebb26e4b16a48ab8a3ac91ddec
Source dataset
uspto-grants-2010_10
Patent number
US07816533B2

Reaction notes

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