HCID 21419586, compound → Bis(3-piperidinopropyl)fluorene-2,7-dicarboxylate dihydrochloride

HRID 441627Notes

Reaction equation

HRID 441627 reaction equation
[ClH:1].Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]([C:15]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][C:21]([C:28]([O:30][CH2:31][CH2:32][CH2:33][N:34]5[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]5)=[O:29])=[CH:22][CH:23]=4)[C:18](=O)[C:17]=3[CH:16]=2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O.[Pd]>[ClH:1].[ClH:1].[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]([C:15]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][C:21]([C:28]([O:30][CH2:31][CH2:32][CH2:33][N:34]5[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]5)=[O:29])=[CH:22][CH:23]=4)[CH2:18][C:17]=3[CH:16]=2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 21419586HCID 21419586, compound

Product 1

HCID 86733059Bis(3-piperidinopropyl)fluorene-2,7-dicarboxylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 20.0 g (0.04 mole) of bis(3-piperidinopropyl)-9-oxofluorene-2,7-dicarboxylate dihydrochloride in water to make a total volume of 240 ml is hydrogenated over 8.0 g of 10% palladium on charcoal for 2 days at 53° C. on a Parr hydrogenation apparatus. The mixture is decanted from the catalyst, filtered through filter aid, treated with charcoal and refiltered. The solution is made basic to phenolphthalein with 20% sodium hydroxide and is extracted three times with CHCl3. The combined extracts are washed twice with water, dried over anhydrous sodium sulfate and filtered. The filtrate is made acidic to Congo Red with ethereal HCl. Most of the solvent is removed on a steam bath under vacuum, and the resulting solid is recrystallized from methanol-ether and from absolute ethanol and vacuum dried to give bis(3-piperidinopropyl)fluorene-2,7-dicarboxylate dihydrochloride.

Workup

  1. customThe mixture is decanted from the catalyst
  2. filtrationfiltered
  3. filtrationthrough filter aid
  4. additiontreated with charcoal
  5. extractionis extracted three times with CHCl3
  6. washThe combined extracts are washed twice with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customMost of the solvent is removed on a steam bath under vacuum
  10. customthe resulting solid is recrystallized from methanol-ether and from absolute ethanol and vacuum
  11. customdried

Sources & evidence

ORD record
ord-6721b109d71c436aa9ae812c58c430bd
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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