Acetophenone → HCID 14409711, compound

HRID 2308032Notes

Reaction equation

HRID 2308032 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C:10]1([C@@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[C:4]1([CH2:1][CH:2]=[N:18][C@H:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:17])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7410AcetophenoneHCID 758181-Phenethylamine, (-)-

Product 1

HCID 14409711HCID 14409711, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

At first, zinc chloride (0.14 g, 1 mmol) was added to a toluene solution (100 ml) containing 12.0 g (100 mmol) of acetophenone (1a) as a ketone and 13.3 g (110 mmol) of (S)-1-phenylethylamine ((S)-2a) as an optically active primary amine, followed by heating under reflux for 20 hr and by removing water (formed as a by-product) with a Dean-Stark tube during the reaction. Then, the reaction liquid after the reaction was washed with a 1N NaOH, followed by washing with 1N ammonium chloride aqueous solution, then drying with sodium sulfate anhydride, then filtration, then concentration, and then drying under vacuum, thereby obtaining 22.5 g of (S)-N-(phenylethylidene)-1-phenylethylamine ((S)-3aa, purity: 99%, yield: 100%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 hr
  3. customby removing water (
  4. customformed as a by-product) with a Dean-Stark tube
  5. customduring the reaction
  6. customThen, the reaction liquid after the reaction
  7. washwas washed with a 1N NaOH
  8. washby washing with 1N ammonium chloride aqueous solution
  9. dry with materialdrying with sodium sulfate anhydride
  10. filtrationfiltration
  11. concentrationconcentration
  12. customdrying under vacuum

Sources & evidence

ORD record
ord-eae62e1717524a20b72b63c4c81f5128
Source dataset
uspto-grants-2004_12
Patent number
US06833468B2

Reaction notes

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