3-Methylpyridine → 3-Methyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromide

HRID 84341Notes

Reaction equation

HRID 84341 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1>>[Br-:1].[CH3:27][C:23]1[CH:22]=[N+:21]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 79703-MethylpyridineHCID 119534943-(13-Bromo-tridecyl)-pyridine

Product 1

HCID 247810993-Methyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromideYield 65%

Procedure

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 3-picoline (5 ml), and the mixture was heated at 50 C overnight. The excess picoline was removed in vacuum, and the resulting residue was partitioned between water and ether. The aqueous layer was washed extensively with ether until no picoline left in the aqueous layer, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (65%). 1HNMR (300 MHz, CDCl3, ppm), 9.36 (s, 1H), 9.22 (d, J=5.4, 1H), 8.44 (br, 2H), 8.21 (d, J=7.5, 1H), 7.97 (m, 1H), 7.54 (d, 7.2, 1H), 7.24-7.24 m, 1H), 4.96 (t, J=7.2, 2H), 2.58-2.65 M, 5H), 2.00-2.07 (m, 4H), 1.58-1.60 (m, 2H), 1.20-1.36 (m, 16H); 13CNMR, 148.76, 146.10, 145.58, 144.77, 142.38, 139.83, 137.29, 127.80, 123.98, 62.28, 58.71, 33.31, 32.36, 31.32, 29.80, 29.74, 29.64, 29.38, 29.35, 26.45, 19.15, 18.81.

Workup

  1. temperaturethe mixture was heated at 50 C overnight
  2. customThe excess picoline was removed in vacuum
  3. customthe resulting residue was partitioned between water and ether
  4. washThe aqueous layer was washed extensively with ether until no picoline
  5. waitleft in the aqueous layer
  6. extractionthe aqueous layer was extracted with chloroform
  7. customThe chloroform was removed

Sources & evidence

ORD record
ord-47297552dfdc4151bebc7cb2733d49c0
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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