Methyl iodide → 1-[(2-Methoxynaphth-3-yl)-N-methylaminocarbonyl]-4-(3,5-dimethylphenyl)piperazine

HRID 1841508Notes

Reaction equation

HRID 1841508 reaction equation
[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[H-].[Na+].[CH3:32]I>CN(C)C=O>[CH3:1][O:2][C:3]1[C:12]([N:13]([CH3:32])[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[C:24]([CH3:29])[CH:25]=[C:26]([CH3:28])[CH:27]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 234462211-[(2-Methoxynaphth-3-yl)aminocarbonyl]-4-(3,5-dimethylphenyl)piperazine

Product 1

HCID 234463591-[(2-Methoxynaphth-3-yl)-N-methylaminocarbonyl]-4-(3,5-dimethylphenyl)piperazineYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-[(2-methoxynaphth-3-yl)aminocarbonyl]-4-(3,5-dimethylphenyl)piperazine (210 mg, 0.54 mmol) dissolved in dimethylformamide (15 ml), 60% sodium hydride (21.5 mg, 0.54 mmol) was added, stirred at room temperature for 15 minutes, and thereto methyl iodide (76.6 mg, 0.54 mmol) was added. The resulting mixture was stirred at room temperature for 6 hours, concentrated under the reduced pressure to remove the solvent and purified by column chromatography to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 6 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the solvent
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-121255f691e34b9baa67cd7e793cfa3f
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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