p-METHYLACETOPHENONE → HCID 88059415, compound

HRID 989462Notes

Reaction equation

HRID 989462 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:22])=O)=[CH:16][CH:15]=1.[C:23]1([C@@H:29]([NH2:31])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:23]1([C:29](=[N:31][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)[CH3:22])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 758181-Phenethylamine, (-)-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 88059415HCID 88059415, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At first, 0.24 g (1.25 mmol) of p-toluenesulfonic acid monohydrate were added to a toluene solution (25 ml) containing 3.35 g (25 mmol) of 4-methylacetophenone (3c) as a ketone and 3.03 g (25 mmol) of (S)-1-phenylethylamine ((S)-2a) as an optically active primary amine, followed by heating under reflux for 24 hr and by removing water (formed as a by-product) with a Dean-Stark tube during the reaction, in order to conduct the reaction. Then, the reaction liquid after the reaction was washed with a saturated sodium hydrogencarbonate aqueous solution, followed by drying with sodium sulfate anhydride, then filtration, then concentration, and then vacuum drying, thereby obtaining as a crude product 5.66 g of (S)-N-(1-phenylethylidene)-1-(4-methylphenyl)-ethylamine ((S)-3ca, yield: 89%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 24 hr
  3. customby removing water (
  4. customformed as a by-product) with a Dean-Stark tube
  5. customduring the reaction
  6. customthe reaction
  7. customThen, the reaction liquid after the reaction
  8. washwas washed with a saturated sodium hydrogencarbonate aqueous solution
  9. dry with materialby drying with sodium sulfate anhydride
  10. filtrationfiltration
  11. concentrationconcentration
  12. customvacuum drying

Sources & evidence

ORD record
ord-1a4e56b10e0849c3b92493c352159675
Source dataset
uspto-grants-2003_10
Patent number
US06639100B2

Reaction notes

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