Potassium Iodide → HCID 19860987, compound

HRID 1165801Notes

Reaction equation

HRID 1165801 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:24])[NH:22][CH2:23][C:19]=2[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][Cl:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CCOCC.C(OCC)(=O)C>[ClH:30].[ClH:30].[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:24])[NH:22][CH2:23][C:19]=2[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])[C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14677303HCID 14677303, compound

Product 1

HCID 19860987HCID 19860987, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

98 mg (0.31 mmole) 1,2,3,6-tetrahydro-4-(2-hydroxyphenyl)-3-oxopyrrolo[3,4-c]carbazole (Example 5) are heated under reflux for 72 hours with 80 mg (0.66 mmole) 3-dimethylaminopropyl chloride, 91 mg (0.66 mmole) potassium carbonate and a spatula tip of potassium iodide in 25 ml acetone. After cooling, it is evaporated and the residue partitioned between water and ethyl acetate. The organic phase is separated off, dried over sodium sulphate, and the residue obtained after evaporation chromatographed on silica gel with NH3 -saturated dichloromethane/methanol 9:1. The fraction with the Rf of 0.6 is isolated, dissolved in an ether/ethyl acetate mixture, and the dihydrochloride precipitated with hydrogen chloride in ether. One obtains 4-[2-(3-dimethylaminopropoxy)phenyl]-6-(3-dimethylaminopropyl)-1,2,3,6-tetrahydro-3-oxopyrrolo[3,4-c]carbazole dihydrochloride in the form of beige crystals which decompose above 170° C.

Workup

  1. temperatureAfter cooling
  2. customit is evaporated
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. customthe residue obtained
  7. customafter evaporation
  8. customchromatographed on silica gel with NH3 -saturated dichloromethane/methanol 9:1
  9. customThe fraction with the Rf of 0.6 is isolated
  10. customthe dihydrochloride precipitated with hydrogen chloride in ether

Sources & evidence

ORD record
ord-872841f9eb5c4ad89e7c629e9b02cc1b
Source dataset
uspto-grants-1990_03
Patent number
US04912107

Reaction notes

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