Dimethylformamide → HCID 70083321, compound

HRID 435104Notes

Reaction equation

HRID 435104 reaction equation
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[H][H].[ClH:18].Cl.[CH3:20][C@H:21]1[NH:26][C@@H:25]([CH3:27])[CH2:24][N:23]([CH2:28][CH2:29][CH2:30][Cl:31])[CH2:22]1.CN(C)C=[O:35]>>[OH2:35].[ClH:31].[ClH:18].[CH3:20][CH:21]1[NH:26][CH:25]([CH3:27])[CH2:24][N:23]([CH2:28][CH2:29][CH2:30][N:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]3[C:15]2=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:22]1.[CH3:20][CH:21]1[NH:26][CH:25]([CH3:27])[CH2:24][N:23]([CH2:28][CH2:29][CH2:30][N:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]3[C:15]2=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:22]1.[ClH:31].[ClH:31]

Participants

6

Reactant 5

HCID 6228Dimethylformamide3×HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 13207837HCID 13207837, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70083321HCID 70083321, compound

Procedure

To a slurry of sodium hydride (1.6 mole) made from 70 g of 57% dispersion in mineral oil and 200 ml of dimethylformamide (DMF) was added a solution of carbazole (83.5 g, 0.5 mole) in DMF (150 ml). When hydrogen was no longer evolved a slurry of 3-(3,5-cis-dimethylpiperazino)propyl chloride dihydrochloride (131 g, 0.5 mole) in DMF (200 ml) was added to the reaction at a slow rate. The reaction was run under nitrogen using a demand system with an oil bubbler. There was some foaming as the slurry was added and the rate of addition was adjusted to keep this to a minimum. After addition was completed the reaction was heated (90°-120°) for 16 to 18 hours, cooled, filtered and stripped of solvent by vacuum distillation. The viscous residue was warmed with 2 liters of 1 N hydrochloric acid, cooled, and washed with ether (500 ml). The ether layer which contained any unreacted carbazole was discarded. The aqueous layer was treated with activated charcoal and filtered through Celite®. The filtrate was made basic to Alkacid® paper using sodium hydroxide, and then extracted with ether four times. Both ether and aqueous layers were clear at the end of the extraction. The ether layer was dried with anhydrous magnesium sulphate or molecular sieves and the hydrochloride salt of 9-[3-(3,5-dimethylpiperazino) propyl]carbazole was precipitated by passing dry hydrogen chloride into the solution. The precipitate was collected and recrystallized from ethyl acetate or ethanol/ether mixture giving 9-[3-(3,5-dimethylpiperazino)propyl]carbazole dihydrochloride hemihydrate (50 g), m.p. 288°-290° C.

Workup

  1. additionwas added to the reaction at a slow rate
  2. additionwas added
  3. additionthe rate of addition
  4. additionAfter addition
  5. temperaturewas heated (90°-120°) for 16 to 18 hours
  6. temperaturecooled
  7. filtrationfiltered
  8. distillationstripped of solvent by vacuum distillation
  9. temperatureThe viscous residue was warmed with 2 liters of 1 N hydrochloric acid
  10. temperaturecooled
  11. washwashed with ether (500 ml)
  12. additionThe aqueous layer was treated with activated charcoal
  13. filtrationfiltered through Celite®
  14. extractionextracted with ether four times
  15. extractionBoth ether and aqueous layers were clear at the end of the extraction
  16. dry with materialThe ether layer was dried with anhydrous magnesium sulphate or molecular sieves
  17. customthe hydrochloride salt of 9-[3-(3,5-dimethylpiperazino) propyl]carbazole was precipitated
  18. customThe precipitate was collected
  19. customrecrystallized from ethyl acetate or ethanol/ether mixture

Sources & evidence

ORD record
ord-594a8eae376f420ba3f101f2bb08dc4b
Source dataset
uspto-grants-1983_08
Patent number
US04400383

Reaction notes

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