Methyl iodide → HCID 10792796, compound

HRID 1387842Notes

Reaction equation

HRID 1387842 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-(piperidinomethyl)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-methyl-phenyl)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-2c29520634194eeb9f5782ded3625a8f
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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