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

HRID 565924Notes

Reaction equation

HRID 565924 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)cinnamoyl-amino)benzyl)piperidine (0.32g) and methyl iodide (0.2ml) in dimethylformamide (5ml) 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) (0.33g) 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-ba2b0ff3218944b3ad742cb425dc1952
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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