Potassium Iodide → 1,1'-(Fluoranthene-3,9-diyl)bis[4-(diethylamino)butan-1-one]--hydrogen chloride (1/2)

HRID 268522Notes

Reaction equation

HRID 268522 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[C:16]([C:17]4[C:22]=2[C:21]=1[CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:14]=[C:13]([C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Cl)[CH:12]=3)=[O:6].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30].[I-].[K+]>O1CCCC1>[ClH:1].[ClH:1].[CH2:29]([N:31]([CH2:32][CH3:33])[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[C:16]([C:17]4[C:22]=2[C:21]=1[CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:14]=[C:13]([C:23](=[O:28])[CH2:24][CH2:25][CH2:26][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[CH:12]=3)=[O:6])[CH3:30]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 515665HCID 515665, compound

Product 1

HCID 681400271,1'-(Fluoranthene-3,9-diyl)bis[4-(diethylamino)butan-1-one]--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.0 g (0.037 mole) of 3,9-bis(4-chlorobutyryl)fluoranthene, 100 ml of diethylamine, 2.0 g of potassium iodide and 100 ml of tetrahydrofuran (THF) is heated at reflux with stirring for 3 days and filtered. The filtrate is poured onto ice water and the oil which separates is decanted and dissolved in ether. The ether solution is washed with a water-saturated sodium chloride solution, dried over magnesium sulfate and filtered. The filtrate is acidified with ethereal HCl, and the resulting precipitate is recrystallized twice from methanol-butanone to yield 3,9-bis(4-diethylaminobutyryl)fluoranthene dihydrochloride. M.P. 236°-239°C.

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. additionThe filtrate is poured onto ice water
  4. customthe oil which separates is decanted
  5. dissolutiondissolved in ether
  6. washThe ether solution is washed with a water-saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe resulting precipitate is recrystallized twice from methanol-butanone

Sources & evidence

ORD record
ord-a4ab6c152c884c3686a65f875dc0fac8
Source dataset
uspto-grants-1976_03
Patent number
US03947593

Reaction notes

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