Toluene → 1-(5-Cyclohexyl-pentyl)-3-phenylquinolinium iodide

HRID 2063937Notes

Reaction equation

HRID 2063937 reaction equation
[C:1]1([NH:7][C:8]2C=N[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]1(C)C=CC=CC=1>CCOCC>[I-:18].[CH:24]1([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N+:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:30]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 561241Benzene, (5-iodopentyl)-HCID 11117560N-phenylquinolin-3-amine

Product 1

HCID 573883581-(5-Cyclohexyl-pentyl)-3-phenylquinolinium iodide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of phenylquinolin-3-yl-amine (100 mg, 0.46 mmol) in toluene (2 ml) and 5-iodopentylbenzene (373 mg, 1.36 mmol) in sealed pressure tube was stirred at 110° C. for 24 hours. The reaction mixture was allowed to cool to room temperature, diluted with Et2O (15 ml), and the resulting precipitate was filtered and washed with Et2O (3×20 ml). The crude product was purified by column chromatography using MeOH/Et2O as eluent. The pure product was an orange solid (75 mg). Mp: 140-141° C.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with Et2O (3×20 ml)
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-25b06205ad914ce18553405bcfa448f8
Source dataset
uspto-grants-2012_10
Patent number
US08288410B2

Reaction notes

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