Pyridine → N,N'-Octane-1,8-diyl-bis-pyridinium Diiodide

HRID 1036574Notes

Reaction equation

HRID 1036574 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]I.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[I-:1].[I-:1].[CH2:2]([N+:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 906051,8-Diiodooctane

Product 1

HCID 11421112N,N'-Octane-1,8-diyl-bis-pyridinium DiiodideYield 93%

Conditions

Temperature
65 °C

Procedure

1,8-Diiodooctane (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 yellow solid was isolated in a 93% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.11 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.59 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.28 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.6, 28.1, 25.2.

Workup

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

Sources & evidence

ORD record
ord-f1976dd19f03446e9fac37be073d329f
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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