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

HRID 1387813Notes

Reaction equation

HRID 1387813 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 (3 ml) was dissolved N-[4-(4-benzyl-piperidino-methyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide (150 mg), 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(100 ml), 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) (141 mg, ratio of isomers=19:81) as colorless crystals.

Workup

  1. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-9103aa4b88fd4bcabcc693a8a14c0eb2
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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