Sodium borohydride → Bis(3-piperidinopropyl) 9-hydroxyfluorene-2,7-dicarboxylate dihydrochloride hydrate

HRID 441628Notes

Reaction equation

HRID 441628 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:40])[C:17]=3[CH:16]=2)=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[BH4-].[Na+]>O>[OH2:12].[ClH:1].[ClH:1].[OH:40][CH:18]1[C:19]2[CH:20]=[C:21]([C:28]([O:30][CH2:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:29])[CH:22]=[CH:23][C:24]=2[C:25]2[C:17]1=[CH:16][C:15]([C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:14])=[CH:27][CH:26]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21419586HCID 21419586, compound

Product 1

HCID 68123551Bis(3-piperidinopropyl) 9-hydroxyfluorene-2,7-dicarboxylate dihydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 10.3 g (0.020 mole) of bis(3-piperidinopropyl)-9-oxofluorene-2,7-dicarboxylate dihydrochloride in 350 ml of warm water is cooled to room temperature and added to 3 g (0.079 mole) of NaBH4 in 15 ml of water with swirling. The resulting product is extracted 5 times with ether, and the combined ether extracts are washed with water, then with NaCl solution, and dried over anhydrous MgSO4. The mixture is filtered, the filtrate treated with ethereal HCl and most of the solvent distilled off. The residue is dissolved in 50 ml of hot ethanol, filtered through filter aid and the filtrate refrigerated. The crystallized solid is filtered off and is recrystallized twice from ethanol to give bis(3-piperidinopropyl) 9-hydroxyfluorene-2,7-dicarboxylate dihydrochloride hydrate.

Workup

  1. extractionThe resulting product is extracted 5 times with ether
  2. washthe combined ether extracts are washed with water
  3. dry with materialwith NaCl solution, and dried over anhydrous MgSO4
  4. filtrationThe mixture is filtered
  5. additionthe filtrate treated with ethereal HCl and most of the solvent
  6. distillationdistilled off
  7. dissolutionThe residue is dissolved in 50 ml of hot ethanol
  8. filtrationfiltered
  9. filtrationthrough filter aid
  10. filtrationThe crystallized solid is filtered off
  11. customis recrystallized twice from ethanol

Sources & evidence

ORD record
ord-43f3833bb8dc40ccaba60a0317e4b766
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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