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1-Chloro-2-(diethylamine)ethane hydrochloride → 2,7-Bis(2-diethylaminoethoxy)fluorene dihydrochloride

HRID 268516
Notes
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Reaction equation

HRID 268516 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][Cl:6])[CH3:2].Cl.[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14][Cl:15])[CH3:11].[OH:18][C:19]1[CH:31]=[CH:30][C:29]2[C:28]3[C:23](=[CH:24][C:25]([OH:32])=[CH:26][CH:27]=3)[CH2:22][C:21]=2[CH:20]=1.C[O-].[Na+]>C1(C)C=CC=CC=1>[ClH:6].[ClH:15].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][O:18][C:19]1[CH:31]=[CH:30][C:29]2[C:28]3[C:23](=[CH:24][C:25]([O:32][CH2:14][CH2:13][N:12]([CH2:10][CH3:11])[CH2:16][CH3:17])=[CH:26][CH:27]=3)[CH2:22][C:21]=2[CH:20]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 13364Diethylaminoethyl chlorideHCID 10942334Sodium MethoxideHCID 149383839H-Fluorene-2,7-diol

Product 1

HCID 124459932,7-Bis(2-diethylaminoethoxy)fluorene dihydrochloride

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
2×

Procedure

A solution of 2-diethylaminoethyl chloride [obtained from 12.9 g (0.075 mole) of 2-diethylaminoethyl chloride hydrochloride] in 100 ml of toluene (dried over molecular sieves) 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 (dried over molecular sieves). This mixture is refluxed with stirring for three hours. Upon cooling the mixture is filtered to remove the precipitated sodium chloride. The toluene solution is washed three times with water, then once with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. This mixture is filtered and the filtrate acidified to Congo Red with ethereal hydrogen chloride. The solid which precipitates is filtered, dissolved in butanone with enough methanol added to effect solution, decolorized with charcoal, and the product obtained at 80°C under vacuum, 2,7-bis(2-diethylaminoethoxy)fluorene dihydrochloride. M.P. 213°-216°C.

Workup

  1. temperatureThis mixture is refluxed
  2. temperatureUpon cooling the mixture
  3. filtrationis filtered
  4. customto remove the precipitated sodium chloride
  5. washThe toluene solution is washed three times with water
  6. dry with materialonce with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  7. filtrationThis mixture is filtered
  8. customThe solid which precipitates
  9. filtrationis filtered
  10. dissolutiondissolved in butanone with enough methanol
  11. additionadded to effect solution

Sources & evidence

ORD record
ord-a68ca0459eb84c6498502e2289b5145e
Source dataset
uspto-grants-1976_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03947593

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes