Ethanol → HCID 21419586, compound

HRID 441626Notes

Reaction equation

HRID 441626 reaction equation
[CH:1]1[C:13]2[C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:15]([Cl:17])=[O:16])[CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:18](Cl)=[O:19].[CH2:21]([OH:23])[CH3:22].[N:24]1([CH2:30][CH2:31][CH2:32][OH:33])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[ClH:17].[ClH:17].[N:24]1([CH2:30][CH2:22][CH2:21][O:23][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][C:9]([C:15]([O:33][CH2:32][CH2:31][CH2:30][N:24]5[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:16])=[CH:8][CH:7]=4)[C:12](=[O:14])[C:13]=3[CH:1]=2)=[O:19])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 702EthanolHCID 66032Piperidine-1-propanolHCID 214196159-Oxo-fluorene-2,7-dicarbonyl chloride

Product 1

HCID 21419586HCID 21419586, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 30.5 g (0.12 mole) of fluoren-9-one-2,7-dicarbonyl chloride in 1 liter of dry chloroform free from ethanol is stirred and treated with 37.5 g (0.26 mole) of 3-piperidino-1-propanol resulting in a mildly exothermic reaction. The resulting mixture is stirred and refluxed for two hours, cooled to room temperature, filtered, and the filtrate washed three times with 250 ml portions of saturated sodium bicarbonate solution. The chloroform solution is then 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 a steam bath under vacuum, and the residue is dissolved in butanone. The solution is made acidic to Congo Red with ethereal HCl causing the product to precipitate as a yellow crystalline solid. The solid is filtered, recrystallized from butanone-methanol and dried to give bis(3-piperidinopropyl)-9-oxofluorene-2,7-dicarboxylate dihydrochloride, M.P. 293°-295° C. (dec.).

Workup

  1. stirringThe resulting mixture is stirred
  2. temperaturerefluxed for two hours
  3. filtrationfiltered
  4. washthe filtrate washed three times with 250 ml portions of saturated sodium bicarbonate solution
  5. washThe chloroform solution is then washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customMost of the solvent is removed from the filtrate on a steam bath under vacuum
  9. dissolutionthe residue is dissolved in butanone
  10. customto precipitate as a yellow crystalline solid
  11. filtrationThe solid is filtered
  12. customrecrystallized from butanone-methanol
  13. customdried

Sources & evidence

ORD record
ord-a383836dbd5243eaa6661fd191733b2c
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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