N,N-Dimethylethylenediamine → HCID 19808732, compound

HRID 374033Notes

Reaction equation

HRID 374033 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CC1C=CC(N2[C:30](=[O:31])[C:29]3[C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[C:25]([O:32][CH3:33])[CH:26]=5)[N:21](COC)[C:20]=4[C:19]([CH2:37][CH2:38][CH3:39])=[CH:18][C:17]=3[C:15]2=[O:16])=CC=1>>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][N:5]1[C:30](=[O:31])[C:29]2[C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:32][CH3:33])[CH:26]=4)[NH:21][C:20]=3[C:19]([CH2:37][CH2:38][CH3:39])=[CH:18][C:17]=2[C:15]1=[O:16]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 19808838HCID 19808838, compound

Product 1

HCID 19808732HCID 19808732, compoundYield 67%

Procedure

1.0 ml of N,N-dimethylethylenediamine was added to 300 mg of N-(4-methylphenyl)-6-methoxy-9-methoxymethyl-1-propylcarbazole-3,4-dicarboximide. The mixture was refluxed for 30 minutes and then concentrated to dryness under reduced pressure. To the residue were added 15 ml of methanol and 1.5 ml of concentrated hydrochloric acid. The mixture was refluxed for 30 minutes. The solvent was removed y distillation under reduced pressure. The residue was mixed with 50 ml of ethyl acetate and 20 ml of an aqueous saturated sodium hydrogencarbonate solution to dissolve the residue. 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 n-propanol to obtain 180 mg (yield: 67%) of N-(2-dimethylaminoethyl)-6-methoxy-1-propylcarbazole-3,4-dicarboximide as yellow needles.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. concentrationconcentrated to dryness under reduced pressure
  3. additionTo the residue were added 15 ml of methanol and 1.5 ml of concentrated hydrochloric acid
  4. temperatureThe mixture was refluxed for 30 minutes
  5. customThe solvent was removed
  6. distillationy distillation under reduced pressure
  7. additionThe residue was mixed with 50 ml of ethyl acetate and 20 ml of an aqueous saturated sodium hydrogencarbonate solution
  8. dissolutionto dissolve the residue
  9. customThe organic layer was separated
  10. washwashed with an aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-149f43194fb3418eac97f3a603102021
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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