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

HRID 565899Notes

Reaction equation

HRID 565899 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 (3ml) was dissolved 7-(4-methylphenyl)-N-[4-(thiomorpholinomethyl)phenyl]-3,4-dihydro-naphthalene-2-carboxamide (160mg), 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 (100ml). The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give 4-methyl-4-[4-[7-(4-methyl-phenyl)-3,4-dihydro-naphthalene-2-carboxamido]benzyl]-thiomorpholinium iodide (Compound 55) (165mg) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-9b645eaeebbc44deae3d0d4330985fc3
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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