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

HRID 565923Notes

Reaction equation

HRID 565923 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 (0.25g) 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 to give 1-methyl-1-(4-(3-(4-fluorophenyl)cinnamoylamino)-benzyl)piperidinium iodide (Compound 87) (0.27g) 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-52ed892f85d04802acc85618f9cad1dd
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

Loading…