Potassium Carbonate → trans-3'-[N-Cyclopropyl-N-(6,6-dimethyl-2-hepten-4-ynyl)aminomethyl]acetophenone

HRID 1356789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356789
[CH:1]1([NH:4][CH2:5][C:6]2[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH:23]=[CH:24][C:25]#[C:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[CH:1]1([N:4]([CH2:5][C:6]2[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH2:22]/[CH:23]=[CH:24]/[C:25]#[C:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 185094213'-(N-Cyclopropylaminomethyl)acetophenoneHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Produkt 1

HCID 18509435trans-3'-[N-Cyclopropyl-N-(6,6-dimethyl-2-hepten-4-ynyl)aminomethyl]acetophenoneAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3′-(N-cyclopropylaminomethyl)acetophenone (0.35 g; 1.85 mmol) and potassium carbonate (0.36 g; 2.64 mmol) were added to N,N-dimethylformamide (15 ml). While the mixture was stirred in an ice bath, 1-bromo-6,6-dimethyl-2-hepten-4-yn (0.35 g; 1.76 mmol) in N,N-dimethylformamide (5 ml) was added dropwise. After completion of the addition, the mixture was removed from the ice bath, and stirred for 18 hours at room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.33 g of the target compound (yield: 60.6%).

Aufarbeitung

  1. additionAfter completion of the addition
  2. customthe mixture was removed from the ice bath
  3. stirringstirred for 18 hours at room temperature
  4. additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
  5. extractionfollowed by extraction with ethyl acetate (100 ml)
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-0c5815ba454d49eea12a40b61d45e2df
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586633B1

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