Hydrochloric Acid → 1-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanone

HRID 30607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30607
Br[C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[CH2:7][N:8]([CH3:10])[CH3:9].[CH2:14]([O:18]C=C)[CH2:15]CC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:9][N:8]([CH2:7][C:6]1[CH:11]=[C:2]([C:14](=[O:18])[CH3:15])[CH:3]=[CH:4][C:5]=1[O:12][CH3:13])[CH3:10]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 8818661-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine

Produkt 1

HCID 8170251-(3-((Dimethylamino)methyl)-4-methoxyphenyl)ethanoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(5-Bromo-2-methoxy-benzyl)-dimethyl-amine (29 mmol), Butoxy-ethene (100 mmol), Palladium acetate (0.9 mmol), 1,3-Bis(diphenylphosphino)propane (1.8 mmol), and potassium carbonate were suspended in DMF (50 ml) and H2O under argon. Heated at 80° C. overnight. Poured into hydrochloric acid (2 M) and stirred for 1 hour. The mixture was adjusted to basic pH and extracted with CH2Cl2. The organic phase was evaporated on celite and the residue was purified by flash chromatography to give the title product as orange oil in 42% yield. 1H-NMR (CDCl3) δ 7.90 (s, 1H), 7.88 (dd, 1H), 6.89 (d, 1H), 3.88 (s, 3H), 3.44 (s, 2H), 2.55 (s, 3H), 2.25 (s, 6H).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was evaporated on celite
  3. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a917ce6dcd2d4fe08b04825b251cbac2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423181B2

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