Sodium Hydroxide → 2,7-Bis(2-piperidinoethoxy)fluoren-9-one dihydrochloride

HRID 441633Notes

Reaction equation

HRID 441633 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[ClH:17].[N:18]1([CH2:24][CH2:25][Cl:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[ClH:26].[ClH:17].[N:18]1([CH2:24][CH2:25][O:1][C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([O:15][CH2:25][CH2:24][N:18]5[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]5)=[CH:9][CH:10]=4)[C:5](=[O:16])[C:4]=3[CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 43541812,7-Dihydroxyfluoren-9-one

Product 1

HCID 136123992,7-Bis(2-piperidinoethoxy)fluoren-9-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5.3 g (0.025 mole) of 2,7-dihydroxyfluoren-9-one in 100 ml of toluene, 16.2 g (0.088 mole) of 2-piperidinoethylchloride hydrochloride and 5.0 g (0.125 mole) of sodium hydroxide in 40 ml of water is heated at reflux for 15 hours with stirring. Upon cooling, the layers are separated. The toluene layer is washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate is acidified to Congo Red with ethereal HCl, and the resulting precipitate is collected, washed with ether and recrystallized from butanone-methanol to give 2,7-bis(2-piperidinoethoxy)fluoren-9-one dihydrochloride, M.P. 304°-306° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 hours
  3. temperatureUpon cooling
  4. customthe layers are separated
  5. washThe toluene layer is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe resulting precipitate is collected
  9. washwashed with ether
  10. customrecrystallized from butanone-methanol

Sources & evidence

ORD record
ord-d268194991154a7e9368e3ceae7d7c3e
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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