Carbazole → N-pentenyl-carbazole

HRID 1108199Notes

Reaction equation

HRID 1108199 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].[Cl-].C([NH+](CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[CH:15]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[CH:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 707041-Pentene, 5-bromo-HCID 12698378Triethylazanium chloride

Product 1

HCID 3813390N-pentenyl-carbazoleYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbazole (30.1 g, 0.18 mol), 5-bromo-1-pentene (25.5 g, 0.17 mol), and triethylammonium chloride (6 g, 0.026 mol) were combined in tetrahydrofuran (200 mL), and a solution of sodium hydroxide (14 g, 0.35 mol) in water (60 mL) was added. The mixture was heated at reflux with stirring for 6 hours, then cooled to room temperature and left overnight. The aqueous layer was separated and the organic phase was concentrated to dryness. The crude product was redissolved in diethyl ether (1000 mL) and washed with water (2×50 mL), dried (Na2SO4,) and then concentrated in vacuo. Recrystallization from methanol afforded N-pentenylcarbazole as cream-colored needles (27.6 g, 65%), m.p.=47° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. waitleft overnight
  4. customThe aqueous layer was separated
  5. concentrationthe organic phase was concentrated to dryness
  6. dissolutionThe crude product was redissolved in diethyl ether (1000 mL)
  7. washwashed with water (2×50 mL)
  8. dry with materialdried (Na2SO4,)
  9. concentrationconcentrated in vacuo
  10. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f706a8e4b2994b4a9da80fb9d0d410dc
Source dataset
uspto-grants-2000_05
Patent number
US06066426

Reaction notes

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