Methyl iodide → 4-Methyl-4-[4-[7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-thiomorpholinium iodide

HRID 2228096Notes

Reaction equation

HRID 2228096 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][N:28]5[CH2:33][CH2:32][S:31][CH2:30][CH2:29]5)=[CH:23][CH:22]=4)=[O:19])=[CH:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[I:35].[C:36](OCC)(=O)C>CN(C=O)C>[I-:35].[CH3:36][N+:28]1([CH2:27][C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:18]([C:14]3[CH2:13][CH2:12][C:11]4[C:16](=[CH:17][C:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=5)=[CH:9][CH:10]=4)[CH:15]=3)=[O:19])=[CH:22][CH:23]=2)[CH2:33][CH2:32][S:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 184725127-(4-methylphenyl)-N-[4-(thiomorpholinomethyl)phenyl]-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 184725544-Methyl-4-[4-[7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-thiomorpholinium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3 ml) was dissolved 7—(4-methylphenyl)-N-[4—(thiomorpholinomethyl)phenyl]-3,4-dihydronaphthalene-2-carboxamide (160 mg), and to the mixture was added methyl iodide (66 μl). The mixture was stirred at room temperature for 17 hours, and to the mixture was added ethyl acetate (100 ml). The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give 4-methyl-4-[4-[7—(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-thiomorpholinium iodide (Compound 55) (165 mg) as colorless crystals.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-8d1fed6d07c942929085aed79a64e6e2
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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