Sodium Methoxide → 2,7-Bis(4-piperidinobutoxy)fluorene dihydrochloride

HRID 1578645Notes

Reaction equation

HRID 1578645 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][Cl:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][C:19]([OH:26])=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1.[CH3:27][O-:28].[Na+]>C1(C)C=CC=CC=1>[ClH:11].[ClH:11].[N:1]1([CH2:7][CH2:8][CH2:9][CH2:27][O:28][C:13]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][C:19]([O:26][CH2:10][CH2:9][CH2:8][CH2:7][N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[CH:20][CH:21]=4)[CH2:16][C:15]=3[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 149383839H-Fluorene-2,7-diolHCID 225682694-Piperidinobutyl chloride

Product 1

HCID 214196232,7-Bis(4-piperidinobutoxy)fluorene dihydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 13.1 g (0.075 mole) of 4-piperidinobutyl chloride in 100 ml of toluene is added to a mixture of 4.9 g (0.025 mole) of 2,7-dihydroxyfluorene and 2.7 g (0.05 mole) of sodium methoxide in 200 ml of toluene. The mixture is refluxed with stirring for 12 hours. Upon cooling, the mixture is filtered to remove the precipitated sodium chloride. The toluene solution is washed with water, then with sodium chloride solution and dried over anhydrous magnesium sulfate. This mixture is filtered and the filtrate acidified to Congo Red with ethereal HCl. Teh precipitate is collected and recrystallized from butanonemethanol to give 2,7-bis(4-piperidinobutoxy)fluorene dihydrochloride.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureUpon cooling
  3. filtrationthe mixture is filtered
  4. customto remove the precipitated sodium chloride
  5. washThe toluene solution is washed with water
  6. dry with materialwith sodium chloride solution and dried over anhydrous magnesium sulfate
  7. filtrationThis mixture is filtered
  8. customTeh precipitate is collected
  9. customrecrystallized from butanonemethanol

Sources & evidence

ORD record
ord-7aad0cee384b4599896f7dcaabd8c7c0
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

Loading…