Methyl iodide → 4-Benzyl-1-methyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-piperidinium iodide

HRID 565881Notes

Reaction equation

HRID 565881 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][C:28]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[I:42].[C:43](OCC)(=O)C>CN(C=O)C>[I-:42].[CH2:1]([CH:8]1[CH2:13][CH2:12][N+:11]([CH3:43])([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][C:28]([C:34]5[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=5)=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 18472459N-[4-(4-benzylpiperidinomethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 184725824-Benzyl-1-methyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-piperidinium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3ml) was dissolved N-[4-(4-benzyl-piperidino-methyl)-phenyl]-7-(4-methylphenyl)-3,4-dihydro-naphthalene-2-carboxamide (150mg), and to the mixture was added methyl iodide (53 μl). The mixture was stirred at room temperature for 23 hours. To the reaction mixture was added ethyl acetate (100ml), and the resulting precipitate was filtered to give 4-benzyl-1-methyl-1-[4-[7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]-piperidinium iodide (Compound 36) (141mg, ratio of isomers=19:81) as colorless crystals.

Workup

  1. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-7152d68605864498a592b1dd67164e23
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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