Methyl iodide → 1-Methyl-1-(4-(3-(4-methoxyphenyl)cinnamoylamino)benzyl)piperidinium iodide

HRID 1277100Notes

Reaction equation

HRID 1277100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=2)[CH:12]=[CH:13][C:14]([NH:16][C:17]2[CH:29]=[CH:28][C:20]([CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][CH:18]=2)=[O:15])=[CH:5][CH:4]=1.[CH3:33][I:34]>CN(C)C=O>[I-:34].[CH3:33][N+:22]1([CH2:21][C:20]2[CH:28]=[CH:29][C:17]([NH:16][C:14](=[O:15])[CH:13]=[CH:12][C:11]3[CH:30]=[CH:31][CH:32]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH:10]=3)=[CH:18][CH:19]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 541118661-(4-(3-(4-Methoxyphenyl)cinnamoylamino)benzyl)piperidine

Product 1

HCID 867561611-Methyl-1-(4-(3-(4-methoxyphenyl)cinnamoylamino)benzyl)piperidinium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-(3-(4-methoxyphenyl)cinnamoylamino)benzyl)piperidine (0.32 g) and methyl iodide (0.2 ml) in dimethylformamide (5 ml) was stirred at room temperature over night. The solvent was evaporated, and to the residue was added ethyl acetate. Precipitated crude crystal was filtered, which were recrystallized from ethanol-hexane to give 1-methyl-1-(4-(3-(4-methoxyphenyl)cinnamoylamino)benzyl)piperidinium iodide (Compound 88) (0.33 g) as pale brown crystals.

Workup

  1. customThe solvent was evaporated
  2. additionto the residue was added ethyl acetate
  3. customPrecipitated crude crystal
  4. filtrationwas filtered
  5. customwhich were recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-e916ea94d7d1464e877b56cd49831b34
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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