1-Propanol, 3-(dibutylamino)- → Bis(3-dibutylaminopropyl)fluoranthene-3,8-dicarboxylate dihydrochloride

HRID 268136Notes

Reaction equation

HRID 268136 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=CC=C(C([Cl:19])=O)C=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:20](Cl)=[O:21])[CH:2]=1.[CH2:23]([N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][OH:31])[CH2:24][CH2:25][CH3:26]>C(Cl)(Cl)Cl>[ClH:19].[ClH:19].[CH2:23]([N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][O:31][C:20]([C:3]1[CH:2]=[CH:1][C:15]2[C:14]3[C:1]([C:8]4[C:16]=2[C:4]=1[CH:5]=[CH:6][CH:7]=4)=[CH:2][C:3]([C:20]([O:31][CH2:30][CH2:29][CH2:28][N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])=[CH:4][CH:9]=3)=[O:21])[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 749051-Propanol, 3-(dibutylamino)-HCID 21419634Fluoranthene-3,8-dicarbonyl chloride

Product 1

HCID 131710106Bis(3-dibutylaminopropyl)fluoranthene-3,8-dicarboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 700 ml of chloroform is added 10.0 g (0.033 mole) of fluoranthene-3,8-dicarbonyl chloride and 12.4 g (0.066 mole) of 3-dibutylaminopropanol and the resulting solution is refluxed overnight. Upon cooling a solid forms which is crystallized from chloroform-ethyl acetate and twice from methanol-ethyl acetate. Further purification is achieved by dissolving the solid in water with subsequent conversion of the solid to the free base by the action of cold 3 N. aqueous potassium hydroxide, extraction of the free base with ether and after drying the ether solution converting the basic ester to the dihydrochloride salt with ethereal-hydrogen chloride. The product is crystallized from methanol-butanone-ether to give bis(3-dibutylaminopropyl)fluoranthene-3,8-dicarboxylate dihydrochloride hemidrate. M.P. 169°-173°C.

Workup

  1. temperaturethe resulting solution is refluxed overnight
  2. temperatureUpon cooling a solid forms which
  3. customis crystallized from chloroform-ethyl acetate and twice from methanol-ethyl acetate
  4. customFurther purification
  5. dissolutionby dissolving the solid in water with subsequent conversion of the solid to the free base by the action of cold 3 N
  6. extractionaqueous potassium hydroxide, extraction of the free base with ether
  7. dry with materialafter drying the ether solution
  8. customThe product is crystallized from methanol-butanone-ether

Sources & evidence

ORD record
ord-50af8344397745be8f575de1921d10f1
Source dataset
uspto-grants-1976_03
Patent number
US03946112

Reaction notes

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