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

HRID 1615039Notes

Reaction equation

HRID 1615039 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].Cl.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23]Cl>CN(C=O)C.O>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:15]1=[CH:3][CH:4]=[CH:5][CH:6]=2

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-Yield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (14.4 g of 60%, 360 mmol) was added portion-wise under argon to a suspension of carbazole 1 (20 g, 119.8 mmol) in dry DMF (200 mL). The mixture was stirred at room temperature for about 1 h until the evolution of the hydrogen ceased. 3-Dimethylaminopropylchloride hydrochloride (28 g, 180 mmol) was added portion-wise at room temperature. The reaction mixture was stirred for 20 min at room temperature, then at 60° C. for 3 hrs, and poured into cold water (500 mL). The product was extracted with EtOAc (2×500 mL). The organic layer was back extracted with 10% HCl (200 mL) and the acidic layer was extracted with EtOAc to remove the unreacted carbazole. Saturated ammonia (200 mL) was added and the product extracted again with EtOAc. Evaporation of the solvent afforded 25 g (99 mmol, 83%) of 9-(2-dimethylaminopropyl)carbazole 2b as a brown oil.

Workup

  1. waitat 60° C. for 3 hrs
  2. extractionThe product was extracted with EtOAc (2×500 mL)
  3. extractionThe organic layer was back extracted with 10% HCl (200 mL)
  4. extractionthe acidic layer was extracted with EtOAc
  5. customto remove the unreacted carbazole
  6. additionSaturated ammonia (200 mL) was added
  7. extractionthe product extracted again with EtOAc
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a97eb48cb0854de3b0768d9fc6c4f2b4
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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