Methyl iodide → HCID 18472648, compound

HRID 565914Notes

Reaction equation

HRID 565914 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:32])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[CH:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:33][I:34]>CN(C=O)C>[I-:34].[CH3:33][N+:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:32])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[CH:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18472227HCID 18472227, compound

Product 1

HCID 18472648HCID 18472648, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (6ml) was dissolved (E)-N-[4-(piperidino-methyl)-phenyl]-3-(2,5-dimethylphenyl)cinnamamide (0.60g), and to the mixture was added methyl iodide (0.60g). The mixture was stirred at room temperature for 20 hours and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give (E)-1-methyl-1-[4-(3-(2,5-dimethylphenyl)cinnamamido)benzyl]-piperidinium iodide (Compound 76) (0.66g) as pale yellow crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ebcd9cd4d08d4d66b7d7dcd25d054c84
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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