HCID 21553589, compound → Bis[5-(dimethylamino)-2,2-dimethylpentyl] 9H-fluorene-2,7-dicarboxylate--hydrogen chloride (1/2)

HRID 268138Notes

Reaction equation

HRID 268138 reaction equation
[ClH:1].Cl.[CH3:3][N:4]([CH3:42])[CH2:5][CH2:6][CH2:7][C:8]([CH3:41])([CH3:40])[CH2:9][O:10][C:11]([C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][C:19]([C:26]([O:28][CH2:29][C:30]([CH3:38])([CH3:37])[CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])=[O:27])=[CH:20][CH:21]=3)[C:16](=O)[C:15]=2[CH:14]=1)=[O:12]>O.[Pd]>[ClH:1].[ClH:1].[CH3:42][N:4]([CH3:3])[CH2:5][CH2:6][CH2:7][C:8]([CH3:41])([CH3:40])[CH2:9][O:10][C:11]([C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][C:19]([C:26]([O:28][CH2:29][C:30]([CH3:37])([CH3:38])[CH2:31][CH2:32][CH2:33][N:34]([CH3:35])[CH3:36])=[O:27])=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1)=[O:12]

Participants

4

Reactant 1

HCID 21553589HCID 21553589, compound

Product 1

HCID 86733175Bis[5-(dimethylamino)-2,2-dimethylpentyl] 9H-fluorene-2,7-dicarboxylate--hydrogen chloride (1/2)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 20.0 g (0.0321 mole) of bis(5-dimethylamino-2,2-dimethylpentyl)-9-oxofluorene-2,7-dicarboxylate dihydrochloride in water (total volume = 240 cc.) is hydrogenated over 8.0 g of 10% palladium on charcoal for 2 days at 53°C on a Parr hydrogenation apparatus. The reaction mixture is decanted from the catalyst, filtered through filtered acid, treated with charcoal and again filtered. This solution is made basic to phenolphthalein with 20% NaOH and extracted 3 times with CHCl3. The combined extracts were washed twice with water, dried over anhydrous Na2SO4, filtered and the filtrate made acid to Congo Red with ethereal HCl. Most of the solvent is removed on the steam bath under vacuum and the resulting solid recrystallized from methanol-ether and from absolute ethanol. Bis(5-dimethylamino-2,2-dimethylpentyl)fluorene-2,7-dicarboxylate dihydrochloride thus obtained is dried for 4 hours under high vacuum at 80°C. M.P. 294°-295°C (gas evolution).

Workup

  1. customThe reaction mixture is decanted from the catalyst
  2. filtrationfiltered
  3. filtrationthrough filtered acid
  4. additiontreated with charcoal
  5. filtrationagain filtered
  6. extractionextracted 3 times with CHCl3
  7. washThe combined extracts were washed twice with water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customMost of the solvent is removed on the steam bath under vacuum
  11. customthe resulting solid recrystallized from methanol-ether and from absolute ethanol

Sources & evidence

ORD record
ord-36e3944fb0894f4c8ed50519d2b6e165
Source dataset
uspto-grants-1976_03
Patent number
US03946112

Reaction notes

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