3,4-Dimethylpyridine → 1-[4-(4-Butyl-phenyl)-butyl]-3,4-dimethyl-pyridinium bromide

HRID 84334

Reaktionsgleichung

Reaktionsgleichung von HRID 84334
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N+:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 114173,4-DimethylpyridineHCID 198479361-(4-Bromo-butyl)-4-butyl-benzene

Produkt 1

HCID 247809421-[4-(4-Butyl-phenyl)-butyl]-3,4-dimethyl-pyridinium bromideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of 3,4-lutidine (3 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no lutidine left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (79%). 1HNMR (300 MHz, CDCl3, ppm), 9.20 (s, 1H), 9.03 (d, J=6.3, 1H), 7.72 (d, J=6.3, 1H), 7.00-7.07 (m, 4H), 4.87 (t, J=7.5, 2H), 2.60 (t, J=7.8, 2H), 2.54 (t, J=7.8, 2H), 2.49 (s, 3H), 2.46 (s, 3H), 1.99-2.04 (m, 2H), 1.50-1.66 (m, 4H), 1.28-1.36 (m, 2H), 0.90 (t, J=7.5, 3H). 13CNMR 157.60, 143.56, 141.92, 140.78, 138.40, 128.63, 128.57, 128.47, 61.00, 35.54, 34.98, 34.04, 31.59, 27.96, 22.73, 20.66, 17.36, 14.31.

Aufarbeitung

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no lutidine
  5. waitleft in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Quellen und Nachweise

ORD-Eintrag
ord-d8a68bdd13b5412caf5bb80c1a96dda1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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