Methyl iodide → HCID 19897890, compound

HRID 1197174Notes

Reaction equation

HRID 1197174 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:5]=1[C:6]1[C:7]([CH2:18][CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:8][CH:9]=[CH:10][C:11]=1[NH:12]2.[CH3:27]I>CN(C)C=O>[CH3:3][C:4]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:5]=1[C:6]1[C:7]([CH2:18][CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:8][CH:9]=[CH:10][C:11]=1[N:12]2[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135555HCID 135555, compound

Product 1

HCID 19897890HCID 19897890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a Suspension of 0.25 ml of 60% sodium hydride (in an oil) in 5 ml of dry N,N-dimethylformamide was added dropwise a solution of 2 g of 5,8-dimethyl-4-(2-di-n-propylaminoethyl)carbazole in 10 ml of dry N,N-dimethyl-formamide, and the mixture was stirred for 30 minutes. To the mixture was added dropwise 1.0 g of methyl iodide, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into ice water and extracted with methylene chloride, and the organic layer was dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was chromato-graphed on silica gel column with hexane - acetone (1 : 3) to give 5,8,9-trimethyl-4-(2-di-n-propylaminoethyl)-carbazole, to which a 4N hydrochloric acid - ethyl acetate solution was added. The formed crystals were collected by filtration to give 1.7 g of 5,8,9-trimethyl-4-(2-di-n-propylaminoethyl)carbazole hydrochloride.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with methylene chloride
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-9a11aa34dbb94349b8cb7ad04df22ab2
Source dataset
uspto-grants-1992_05
Patent number
US05116995

Reaction notes

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