Isopropanol → Bis(3-diethylaminopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

HRID 268139

Reaction equation

HRID 268139 reaction equation
[CH:1](O)([CH3:3])[CH3:2].[CH2:5]([N:7]1[C:19]2[CH:18]=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([C:23]([OH:25])=[O:24])[CH:12]=2)[CH3:6].[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][CH2:31][Cl:32])[CH3:27]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCOCC>[ClH:32].[ClH:32].[CH2:5]([N:7]([CH2:8][CH3:9])[CH2:2][CH2:1][CH2:3][O:24][C:23]([C:11]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:5][CH3:6])[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][C:16]([C:20]([O:22][CH2:31][CH2:30][CH2:29][N:28]([CH2:33][CH3:34])[CH2:26][CH3:27])=[O:21])=[CH:17][CH:18]=3)=[O:25])[CH3:6]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 669183-Chloropropyl(diethyl)amineHCID 37979149-ethyl-9H-carbazole-3,6-dicarboxylic acid

Product 1

HCID 12331707Bis(3-diethylaminopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To 250 ml of isopropanol is added 10.0 g (0.035 mole) of 9-ethylcarbazole-3,6-dicarboxylic acid, 21.2 g (0.14 mole) of 3-diethylaminopropylchloride and 0.5 ml of 60% aqueous benzyltrimethylammonium chloride. The solution is heated at reflux for 2 hours with stirring and then allowed to stir overnight at room temperature. Addition of ether to the reaction mixture gives a crystalline product which is recrystallized twice from methanol-acetone to give bis(3-diethylaminopropyl)-9-ethylcarbazole-3,6-dicarboxylate dihydrochloride. M.P. 233°-234°C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 2 hours
  3. stirringto stir overnight at room temperature
  4. customgives a crystalline product which
  5. customis recrystallized twice from methanol-acetone

Sources & evidence

ORD record
ord-c731bbd411ca405b9cb59a8a9db8cc07
Source dataset
uspto-grants-1976_03
Patent number
US03946112

Linked notes

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