Methyl iodide → HCID 18472325, compound

HRID 1387846Notes

Reaction equation

HRID 1387846 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=4)[CH:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][I:35]>CN(C=O)C>[I-:35].[CH3:34][N+:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=4)[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 18472220HCID 18472220, compound

Product 1

HCID 18472325HCID 18472325, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (6 ml) was dissolved (E)-N-[4-(piperidinomethyl)phenyl]-3-(3-nitrophenyl)cinnamamide (0.59 g), and to the mixture was added methyl iodide (0.57 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-(3-nitro-phenyl)cinnamamido)benzyl]-piperidinium iodide (Compound 77) (0.75 g) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-0aa6b7e76ecf4946a7393fab92e6cd53
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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