2,4-Dimethylpyridine → 1-[4-(4-Butyl-phenyl)-butyl]-2,4-dimethyl-pyridinium bromide

HRID 84333

Reaction equation

HRID 84333 reaction equation
[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])=[CH:18][C:17]=1[CH3:23]>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])=[CH:18][C:17]=2[CH3:23])=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 79362,4-DimethylpyridineHCID 198479361-(4-Bromo-butyl)-4-butyl-benzene

Product 1

HCID 247809401-[4-(4-Butyl-phenyl)-butyl]-2,4-dimethyl-pyridinium bromideYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of 2,4-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), 9.51 (d, J=6.2, 1H), 7.67 (d, J=6.2, 1H), 7.54 (s, 1H), 7.05-7.07 (m, 4H), 4.83 (t, J=7.2, 2H), 2.77 (s, 3H), 2.64 (t, J=7.2, 2H), 2.52-2.58 (m, 5H), 1.87-1.92 (m, 2H), 1.76-1.82 (m, 2H), 1.50-1.58 (m, 2H), 1.29-1.37 (m, 2H), 0.91 (t, J=7.8, 3H).

Workup

  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

Sources & evidence

ORD record
ord-610073acc68b463881d23366af041e57
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Linked notes

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