Carbazole → N-Propylphenylcarbazole

HRID 983375Notes

Reaction equation

HRID 983375 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.BrCCC[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].[CH2:26](N1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:27][CH2:28]CCCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:26]([N:12]1[C:11]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 12503(3-Bromopropyl)benzeneHCID 14798Sodium HydroxideHCID 138604829-Heptyl-9H-carbazole

Product 1

HCID 69731188N-Propylphenylcarbazole

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

N-Propylphenylcarbazole was prepared from carbazole (82.18 g, 0.49 ml), 1-bromo-3-phenylpropane (100 g, 0.50 mol, commercially available from Aldrich, Milwaukee, Wis.), benzyltriethyl ammonium chloride (5.58 g, 0.025 mol), toluene (400 ml), and 50% aqueous NaOH (200 g) according to the procedure described for N-heptylcarbazole. 108 g of the product was obtained as a white solid (77% yield).

Sources & evidence

ORD record
ord-b3bafcb236124613912294b73d6217e3
Source dataset
uspto-grants-2005_03
Patent number
US06864025B2

Reaction notes

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