Pyridine → N,N'-Dodecanediyl-bis-pyridinium dibromide

HRID 1036577Notes

Reaction equation

HRID 1036577 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]Br.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Br-:1].[Br-:1].[CH2:2]([N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 187661,12-Dibromododecane

Product 1

HCID 11202566N,N'-Dodecanediyl-bis-pyridinium dibromideYield 93%

Conditions

Temperature
65 °C

Procedure

1,12-Dibromododecane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting white solid was isolated in a 93% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.15 (2H, d, C2&C6-H), 8.62 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.61 (2H, t, C′1-CH2), 1.88 (2H, m, C′2-CH2), 1.22 (8H, m, C′3-6-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.6, 127.9, 60.7, 30.8, 28.9, 28.8, 28.5, 25.4.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthe product washed five times with dry diethyl ether
  3. customThe resulting white solid was isolated in a 93% yield

Sources & evidence

ORD record
ord-31c1b54ba24844cca3e0c32b52bb3f5a
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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