Isoquinoline → N,N'-Octane-1,8-diyl-bis-isoquinolinium Diiodide

HRID 1036583Notes

Reaction equation

HRID 1036583 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]I.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1>>[I-:1].[I-:1].[CH2:2]([N+:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 8405IsoquinolineHCID 906051,8-Diiodooctane

Product 1

HCID 11285041N,N'-Octane-1,8-diyl-bis-isoquinolinium DiiodideYield 92%

Conditions

Temperature
65 °C

Procedure

1,8-Diiodooctane (mmol) was added to a solution (30 mL) of isoquinoline, 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 an 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.05 (1H, d, C1-H), 8.77 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.35 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.68 (2H, t, C′1-CH2), 2.00 (2H, m, C′2-CH2), 1.30 (4H, m, C′3&4-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 an 92% yield

Sources & evidence

ORD record
ord-f537fd2d7dbf432e9dd18eda101ca873
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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