Carbazole → HCID 58544901, compound

HRID 1615040Notes

Reaction equation

HRID 1615040 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.[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23]Cl)[CH3:20]>CN(C=O)C.O>[CH2:19]([N:21]([CH2:25][CH3:26])[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)[CH3:20]

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 58544901HCID 58544901, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (14.4 g of 60%, 360 mmol, 3 eq) was added portion-wise under argon to a suspension of carbazole (1) (20 g, 119.8 mmol, 1 eq) in dry DMF (200 mL). The mixture was stirred at room temperature for 30 min until the evolution of the hydrogen ceased. 2-Diethylaminoethylchloride hydrochloride (31 g, 180 mmol, 1.5 eq) was added in portion-wise at room temperature. The reaction mixture was stirred for 20 min at room temperature, then at 60° C. for 3 hrs (TLC monitoring), and poured into cold water (1 L). The product was extracted with EtOAc (5×200 mL); the organic layer was back extracted with 10% HCl (400 mL) and acidic layer was extracted with EtOAc to remove the un-reacted carbazole. The pH of aqueous layer was adjusted to about 9 with K2CO3 and the product extracted again with EtOAc. Evaporation of the solvent afforded 29.5 g (93%) of 9-(2-diethylaminoethyl)carbazole (68) as a brown oil.

Workup

  1. waitat 60° C. for 3 hrs (TLC monitoring)
  2. extractionThe product was extracted with EtOAc (5×200 mL)
  3. extractionthe organic layer was back extracted with 10% HCl (400 mL) and acidic layer
  4. extractionwas extracted with EtOAc
  5. customto remove the un-reacted carbazole
  6. extractionthe product extracted again with EtOAc
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8672cb5e200e46c4885b2f0ca28eeb2c
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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