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

HRID 1387855Notes

Reaction equation

HRID 1387855 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 (0.32 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-ac0579d9aa544120b00f5e674a4565e8
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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