Methyl iodide → HCID 22990178, compound

HRID 1169443Notes

Reaction equation

HRID 1169443 reaction equation
[CH3:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C[I:32].[C:33](OCC)(=O)C>CN(C=O)C>[I-:32].[CH3:33][N+:18]1([CH2:17][C:16]2[CH:24]=[CH:25][C:13](/[CH:12]=[CH:11]/[C:10]3[CH:26]=[CH:27][CH:28]=[C:8]([O:7][CH2:6][C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:30][CH:29]=4)[CH:9]=3)=[CH:14][CH:15]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 22990123HCID 22990123, compound

Product 1

HCID 22990178HCID 22990178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (E)-1-[4-[3-(4-methylbenzyloxy)styryl]benzyl]piperidine (150 mg) dissolved in DMF (3 ml) was added methyl iodide (70 μl ), and the resulting mixture was stirred at room temperature for 66 hours. The reaction mixture was mixed with ethyl acetate (100 ml) and the resulting precipitate was collected by filtration and recrystallized from ethyl acetate/methanol to obtain (E)-1-methyl-1-[4-[3-(4-methylbenzyloxy)styryl]benzyl]piperidinium iodide (compound 100) (183 mg) as colorless crystals.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customrecrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-ea3562eb05ca4a638cae3f09886d3497
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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