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

HRID 2228119Notes

Reaction equation

HRID 2228119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=2)[CH:11]=[CH:12][C:13]([NH:15][C:16]2[CH:28]=[CH:27][C:19]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:18][CH:17]=2)=[O:14])=[CH:4][CH:3]=1.[CH3:32][I:33]>CN(C)C=O>[I-:33].[CH3:32][N+:21]1([CH2:20][C:19]2[CH:27]=[CH:28][C:16]([NH:15][C:13](=[O:14])[CH:12]=[CH:11][C:10]3[CH:29]=[CH:30][CH:31]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH:9]=3)=[CH:17][CH:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 539677711-(4-(3-(4-Fluoro-phenyl)cinnamoylamino)benzyl)piperidine

Product 1

HCID 867561601-Methyl-1-(4-(3-(4-fluorophenyl)cinnamoylamino)benzyl)piperidinium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 83 (0.25 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 to give 1-methyl-1—(4—(3—(4-fluorophenyl)cinnamoylamino)benzyl)piperidinium iodide (Compound 87) (0.27 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

Sources & evidence

ORD record
ord-69ff7b9a29c3494aa36567f61ace6f55
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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