Diphenyl Ether → N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximide

HRID 374032Notes

Reaction equation

HRID 374032 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[CH3:14][N:15]([CH3:36])[CH2:16][CH2:17][N:18]1[C:34](=[O:35])[C:33]2[C:32]3[C:31]4[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=4[NH:25][C:24]=3[CH:23]=[CH:22][C:21]=2[C:19]1=[O:20]>[C].[Pd].C(Cl)(Cl)Cl>[CH3:14][N:15]([CH3:36])[CH2:16][CH2:17][N:18]1[C:34](=[O:35])[C:33]2[C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]=3[CH:23]=[CH:22][C:21]=2[C:19]1=[O:20]

Participants

5

Reactant 2

HCID 7583Diphenyl EtherHCID 19808739N-(2-dimethylaminoethyl)-5,6,7,8-tetrahydrocarbazole-3,4dicarboximide

Product 1

HCID 19808710N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximideYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

3.6 g of diphenyl ether and 70 mg of 10% palladium-carbon were added to 180 mg of N-(2-dimethylaminoethyl)-5,6,7,8-tetrahydrocarbazole-3,4dicarboximide. The mixture was refluxed in a nitrogen stream for 15 minutes, and then cooled to room temperature. Thereto was added 40 ml of chloroform. The resulting insoluble material was removed by filtration. The filtrate was mixed with 25 ml of water. The mixture was adjusted to pH 1.0 with 6N hydrochloric acid. The aqueous layer was separated, washed with 10 ml of chloroform, and mixed with 20 ml of chloroform. The mixture was adjusted to pH 7.5 with an aqueous saturated sodium hydrogencarbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to obtain 100 mg (yield: 56%) of N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximide as yellow needles.

Workup

  1. temperatureThe mixture was refluxed in a nitrogen stream for 15 minutes
  2. customThe resulting insoluble material was removed by filtration
  3. additionThe filtrate was mixed with 25 ml of water
  4. customThe aqueous layer was separated
  5. washwashed with 10 ml of chloroform
  6. additionmixed with 20 ml of chloroform
  7. customThe organic layer was separated
  8. washwashed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed by distillation under reduced pressure
  11. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-edbbd9fcb3c746ef88e48e2fc1ac1602
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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