Carbazole → 6-[3-(Dimethylamino)propyl]-8-methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615009Notes

Reaction equation

HRID 1615009 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:8]4[CH2:18][CH2:17][C:16](=[O:19])[C:9]=4[CH:10]=[CH:11][C:12]=3[NH:13][C:14]=2[CH:15]=1.[H-].[Na+].Cl.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.C1C2NC3C(=CC=CC=3)C=2C=CC=1>C(Cl)Cl.O.C(Cl)(Cl)Cl.CO.C(Cl)Cl.C(OCC)(=O)C>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][N:13]1[C:12]2[CH:11]=[CH:10][C:9]3[C:16](=[O:19])[CH2:17][CH2:18][C:8]=3[C:7]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][C:14]1=2

Participants

9

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 709006108-Methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 585449126-[3-(Dimethylamino)propyl]-8-methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolventHCID 21584188Chloroform methanolSolvent

Procedure

Compound 36 (1.0 g, 3.98 mmol) was suspended in CH2Cl2 (10 mL); NaH (0.75 g, 12.0 mmol, 3 eq.) was added. The mixture was stirred at room temperature for 5-10 min; then 3-dimethylamino-1-propyl chloride hydrochloride (0.75 g, 4.74 mmol, 1.2 eq.) was added. The reaction mixture was heated to 70° C., kept at this temperature for 2 h (TLC monitoring, eluent: CH2Cl2-ethyl acetate, 1:1—the presence of initial carbazole, CHCl3-MeOH, 9:1—purity of the product). The resulting mixture was diluted with water, extracted with ethyl acetate, evaporated, and purified on a short thick column with silica gel, eluent: CHCl3-MeOH 99:1→90:10. Yield of 37: 0.84 g (63%).

Workup

  1. temperatureThe reaction mixture was heated to 70° C.
  2. waitkept at this temperature for 2 h
  3. extractionextracted with ethyl acetate
  4. customevaporated
  5. custompurified on a short thick column with silica gel, eluent

Sources & evidence

ORD record
ord-d06fc2c948f64d798c457277b158873a
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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