Hydrochloric Acid → 2,7-Bis(piperidinomethyl)fluorene

HRID 1576969Notes

Reaction equation

HRID 1576969 reaction equation
[N:1]1([CH2:7][C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:15][CH:16]=4)[CH:11](O)[C:10]=3[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>[Pd].O>[N:1]1([CH2:7][C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([CH2:21][N:22]5[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]5)=[CH:15][CH:16]=4)[CH2:11][C:10]=3[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 215099632,7-Bis(piperidinomethyl)fluoren-9-ol

Product 1

HCID 215099762,7-Bis(piperidinomethyl)fluorene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 6.15 g (0.016 mole) of 2,7--bis(piperidinomethyl)fluorene-9-ol, 12.1 ml of 10% hydrochloric acid, sufficient deionized water to bring the total volume to 150 ml, and 3.0 g of 10% palladium on charcoal catalyst is placed in a Paar hydrogenation apparatus and hydrogenated at room temperature for a period of 2 hours and 45 minutes. The resulting mixture is filtered and sufficient 20% sodium hydroxide solution is added to render the mixture basic to phenolphthalein indicator. The reaction mixture is extracted four times with chloroform, the extracts combined, washed twice with deionized water, treated with charcoal, filtered, and the major portion of the solvent removed at atmospheric pressure. The residue is recrystallized twice from methanol and once again from acetone yielding 2,7-bis(piperidinomethyl)fluorene having a m.p. 135°-6°C, λmax0.1N HCl 270, and E1cm1% 807.

Workup

  1. filtrationThe resulting mixture is filtered
  2. additionsufficient 20% sodium hydroxide solution is added to render the mixture basic to phenolphthalein indicator
  3. extractionThe reaction mixture is extracted four times with chloroform
  4. washwashed twice with deionized water
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customthe major portion of the solvent removed at atmospheric pressure
  8. customThe residue is recrystallized twice from methanol and once again from acetone

Sources & evidence

ORD record
ord-b01a0f0483d04e5eacef01cc0a395e1c
Source dataset
uspto-grants-1976_09
Patent number
US03983124

Reaction notes

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