Pyridine → 1-(5-pyridin-1-ium-1-ylpentyl)pyridin-1-ium;diiodide

HRID 1036572Notes

Reaction equation

HRID 1036572 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]I.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[I-:1].[I-:1].[CH2:2]([N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 123541,5-Diiodopentane

Product 1

HCID 112486641-(5-pyridin-1-ium-1-ylpentyl)pyridin-1-ium;diiodideYield 90%

Conditions

Temperature
65 °C

Procedure

1,5-Diiodopentane (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 90% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.14 (2H, d, C2&C6-H), 8.62 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.62 (2H, t, C′1-CH2), 1.92 (2H, m, C′2-CH2), 1.25 (1H, m, C′3-CH2).

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 90% yield

Sources & evidence

ORD record
ord-241a45435eb94dda92d5635714135474
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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