Carbazole → HCID 5147738, compound

HRID 900030Notes

Reaction equation

HRID 900030 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][CH2:18][CH3:19].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCCC1.O>[CH2:15]([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)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 80571-BromopentaneHCID 14798Sodium Hydroxide

Product 1

HCID 5147738HCID 5147738, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Compound (19) can be prepared according to the following procedure. Carbazole (16.7 g, 0.1 mol, commercially available from Aldrich, Milwaukee, Wis.), 1-bromopentane (15.1 g, 0.1 mol, commercially available from Aldrich, Milwaukee, Wis.), and benzyltriethyl ammonium chloride (1.7 g) are dissolved in tetrahydrofuran (60 mL) and a concentrated solution of sodium hydroxide (17 g) in water (17 mL) is added. The mixture is heated at reflux with strong mechanical stirring for 4 hours, then cooled to room temperature and poured into an excess of water. The solid that precipitated is filtered off and the tetrahydrofuran layer is dried (MgSO4) and concentrated to dryness. The combined organic solids were recrystallized to form 9-pentylcarbazole.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux with strong
  3. customThe solid that precipitated
  4. filtrationis filtered off
  5. dry with materialthe tetrahydrofuran layer is dried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customThe combined organic solids were recrystallized

Sources & evidence

ORD record
ord-a1edfdad887d4508a5696276859b2ed8
Source dataset
uspto-grants-2008_04
Patent number
US07358014B2

Reaction notes

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