Methyl iodide → HCID 10792796, compound

HRID 2228108Notes

Reaction equation

HRID 2228108 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:31])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[CH:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][I:33]>CN(C=O)C>[I-:33].[CH3:32][N+:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:31])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[CH:19]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18472477HCID 18472477, compound

Product 1

HCID 10792796HCID 10792796, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (4 ml) was dissolved (E)-N-[4—(piperidino-methyl)phenyl]-3—(4-methylphenyl)cinnamamide (0.41 g), and to the mixture was added methyl iodide (0.43 g). 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—(4-methylphenyl)cinnamamido)benzyl]-piperidinium iodide (Compound 72) (0.51 g) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-02fb81fa903d4815a884babffb9180fe
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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