Methyl iodide → HCID 18472575, compound

HRID 565898Notes

Reaction equation

HRID 565898 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 (3ml) was dissolved 3,4-dihydro-N-[4-(4-hydroxypiperidinomethyl)phenyl]-7-(4-methylphenyl)-naphthalene-2-carboxamide (130mg), 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 (100ml). 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) (138mg, 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-59daab322eae439e95bf5e7a0b10d90a
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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