2,4-Dimethylpyridine → 2,4-Dimethyl-1-(8-phenyl-octyl)-pyridinium bromide

HRID 84318

Reaction equation

HRID 84318 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[CH3:23]>C(#N)C>[Br-:1].[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][N+:16]=1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 79362,4-DimethylpyridineHCID 563758(8-Bromooctyl)benzene

Product 1

HCID 247811072,4-Dimethyl-1-(8-phenyl-octyl)-pyridinium bromideYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(8-Bromo-octyl)-benzene (1 mmol) was added to a solution of 2,4-lutidine (3 mmol) in acetonitrile, and the solution 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 2,4-lutidine was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (70%). 1HNMR (300 MHz, CDCl3, ppm), 9.50 (d, 1H), 7.70 (d, 1H), 7.60 (s, 1H), 7.10-7.30 (dd, 1H), 4.78 (t, 2H), 2.84 (s, 3H), 2.54-2.60 (m, 5H), 1.80-1.92 (m, 2H), 1.50-1.60 (br, 2H), 1.20-1.45 (br, 6H).

Workup

  1. temperaturethe solution 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 2,4-lutidine
  5. waitwas left 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-ae2970e90ced41e2af384030d203cc41
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Linked notes

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