Potassium Iodide → Carbazole, 9-(3-(dimethylamino)propyl)-

HRID 348530Notes

Reaction equation

HRID 348530 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.Cl.[CH3:19][NH:20][CH3:21].C([O-])([O-])=O.[K+].[K+].[I-].[K+]>C(#N)C>[CH3:19][N:20]([CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 147374369-(3-Chloropropyl)-9H-carbazole

Product 1

HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-(3-chloropropyl)carbazole (2.5 g, 10 mmol) was dissolved in acetonitrile (50 mL) in a pressure tube and dimethylamine hydrochloride (12.2 g, 150 mmol, followed by K2CO3 (20.8 g, 150 mmol) and potassium iodide (0.2 g, 1 mmol) were added and the mixture was stirred at room temperature for 7 days, then filtered and the filtrate concentrated in vacuo. The crude was purified by column chromatography (eluting with 5% methanol in dichloromethane) to afford 1.87 g of the title compound.

Workup

  1. additionwere added
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude was purified by column chromatography (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-408fbd6a2a70447f9cd3f57208370935
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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