1-Propanol, 3-(dibutylamino)- → Bis[3-(dibutylamino)propyl] 9-oxo-9H-fluorene-2,7-dicarboxylate--hydrogen chloride (1/2)

HRID 1606584Notes

Reaction equation

HRID 1606584 reaction equation
[O:1]=[C:2]1[C:14]2[CH:13]=[C:12]([C:15]([Cl:17])=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5]([C:18](Cl)=[O:19])=[CH:6][CH:7]=2.[CH2:21]([N:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][OH:29])[CH2:22][CH2:23][CH3:24]>C(Cl)(Cl)Cl>[ClH:17].[ClH:17].[CH2:21]([N:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][O:29][C:18]([C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[C:14](=[CH:13][C:12]([C:15]([O:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:16])=[CH:11][CH:10]=3)[C:2](=[O:1])[C:3]=2[CH:4]=1)=[O:19])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 749051-Propanol, 3-(dibutylamino)-HCID 214196159-Oxo-fluorene-2,7-dicarbonyl chloride

Product 1

HCID 68140824Bis[3-(dibutylamino)propyl] 9-oxo-9H-fluorene-2,7-dicarboxylate--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 30.5 g (0.10 mole) of 9-oxo-fluorene-2,7-dicarbonyl chloride in 1 liter of dry chloroform (ethanol free) is stirred and treated all at once with 37.5 g (0.20 mole) of dry 3-dibutylamino-1-propanol causing a mildly exothermic reaction. The resulting mixture is stirred and refluxed for 2 hours, cooled to room temperature, filtered and the filtrate washed three times with 250 ml portions of a saturated sodium bicarbonate solution. The chloroform solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. Most of the solvent is removed from the filtrate on the steam bath in vacuo and the remaining residue dissolved in butanone. This solution is made acid to Congo red with ethereal HCl causing the desired product to precipitate as a yellow crystalline solid. The bis [3-(dibutylamino)propyl]9-oxo-fluorene-2,7-dicarboxylate dihydrochloride so obtained is filtered, recrystallized from a butanone-methanol mixture and dried. The compound on standing in the atmosphere forms a monohydrate having a m.p. 178.5-179.5° C., λmaxH2O 276, and E 1cm1% 1,370.

Workup

  1. customa mildly exothermic reaction
  2. stirringThe resulting mixture is stirred
  3. temperaturerefluxed for 2 hours
  4. filtrationfiltered
  5. washthe filtrate washed three times with 250 ml portions of a saturated sodium bicarbonate solution
  6. washThe chloroform solution is washed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customMost of the solvent is removed from the filtrate on the steam bath in vacuo
  10. dissolutionthe remaining residue dissolved in butanone
  11. customto precipitate as a yellow crystalline solid

Sources & evidence

ORD record
ord-2cb0514bfe0e49d2a1099c139c022214
Source dataset
uspto-grants-1976_04
Patent number
US03953455

Reaction notes

Loading…