Methyl iodide → HCID 86665673, compound

HRID 868839Notes

Reaction equation

HRID 868839 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][CH:5]=1.[CH3:15][I:16]>C(#N)C>[I-:16].[CH3:1][N+:2]([CH3:15])([CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2762435HCID 2762435, compound

Product 1

HCID 86665673HCID 86665673, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Dimethyl-(4-methyl-1H-indol-3-ylmethyl)-amine (20 g, 98 mmol) is suspended in acetonitrile, and warmed to completely dissolve the material. The reaction is cooled to room temperature and then methyl iodide (9.1 mL, 147 mmol) is added dropwise to the reaction. The reaction is covered with foil and then stirred at room temperature overnight. The reaction is then filtered and the filtrate evaporate in vacuo to give an oil that is taken up in acetonitrile. The white solid is then triturated with acetonitrile and ether, and combined with the original solid to give the title compound that is used without further purification (30 g, 87 mmol, 88%) LC/MS (M++1): 347.

Workup

  1. temperaturewarmed
  2. dissolutionto completely dissolve the material
  3. filtrationThe reaction is then filtered
  4. customthe filtrate evaporate in vacuo
  5. customto give an oil that
  6. customThe white solid is then triturated with acetonitrile and ether

Sources & evidence

ORD record
ord-506eb8760e4b4118a2a54488280a975a
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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