Methyl iodide → HCID 22990076, compound

HRID 1169364Notes

Reaction equation

HRID 1169364 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][O:10][C:11]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:35])[CH:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[CH:23][CH:22]=4)=[O:19])=[CH:14][C:12]=3[CH:13]=2)=[CH:4][CH:3]=1.[CH3:36][I:37]>CN(C=O)C>[I-:37].[CH3:35][N+:28]([CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)([CH3:36])[CH2:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18]([C:15]2[CH:16]=[CH:17][C:11]3[O:10][CH2:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=4)=[CH:13][C:12]=3[CH:14]=2)=[O:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22990184HCID 22990184, compound

Product 1

HCID 22990076HCID 22990076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 3-(4-methylphenyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2H-1-benzopyran-6-carboxamide (80 mg) in DMF (30 ml) was added at room temperature methyl iodide (0.04 ml), and the resulting mixture was stirred for 3 days. After evaporation of the solvent under reduced pressure, ethyl acetate was added to the residue, and the precipitated crystals were collected by filtration to obtain N,N-dimethyl-N-[4-[[3-(4-methylphenyl)-2H-1-benzopyran-6-carbonyl]amino]benzyl]-4-tetrahydropyranylammonium iodide (compound 28) (87 mg) as light yellow crystals.

Workup

  1. customAfter evaporation of the solvent under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ced9a785449e4acb89447cac86ae1928
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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