Methyl iodide → HCID 18472494, compound

HRID 1387983Notes

Reaction equation

HRID 1387983 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:34])[CH:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)=[CH:22][CH:21]=4)=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.[CH3:35][I:36]>CN(C=O)C>[I-:36].[CH3:34][N+:27]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)([CH3:35])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17]([C:14]2[CH:15]=[CH:16][C:10]3[O:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[CH:12][C:11]=3[CH:13]=2)=[O:18])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18472277HCID 18472277, compound

Product 1

HCID 18472494HCID 18472494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methylphenyl)-N-[4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)phenyl]-benzofuran-5-carboxamide (120 mg) in DMF (20 ml) was added at room temperature methyl iodide (0.04 ml), and the mixture was stirred for 24 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethanol. The resulting crystals were collected by filtration to give yellow crystals of N,N-dimethyl-N-[4-[[2-(4-methyl-phenyl)benzofuran-5-carbonyl]amino]-benzyl]-4-tetrahydropyranyl ammonium iodide (Compound 281) (142.1 mg).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added ethanol
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-5796807a5399479a9abd1ec151e6624c
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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