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

HRID 441632Notes

Reaction equation

HRID 441632 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. The precipitate is collected and recrystallized from butanone-methanol 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. customThe precipitate is collected
  9. customrecrystallized from butanone-methanol

Sources & evidence

ORD record
ord-15a595e880fe4472a75ef9a500559476
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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