Methyl iodide → HCID 18472575, compound

HRID 1387830Notes

Reaction equation

HRID 1387830 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][C:22]([C:28]5[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=5)=[CH:23][CH:24]=4)[CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C[I:36].[C:37](OCC)(=O)C>CN(C=O)C>[I-:36].[OH:1][CH:2]1[CH2:3][CH2:4][N+:5]([CH3:37])([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][C:22]([C:28]5[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=5)=[CH:23][CH:24]=4)[CH:19]=3)=[O:17])=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 18472215HCID 18472215, compound

Product 1

HCID 18472575HCID 18472575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3 ml) was dissolved 3,4-dihydro-N-[4-(4-hydroxypiperidinomethyl)phenyl]-7-(4-methylphenyl)-naphthalene-2-carboxamide (130 mg), and to the mixture was added methyl iodide (54 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-hydroxy-1-methyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-piperidinium iodide (Compound 54) (138 mg, ratio of isomers=58:42) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-b3bfd5b731324e5ea28acab031f8d7ca
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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