Ethyl Acetate → 1-Ethyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]piperidinium chloride

HRID 565879Notes

Reaction equation

HRID 565879 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[CH2:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30].C(OCC)(=O)C>CN(C=O)C>[Cl-:1].[CH2:29]([N+:31]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]3[CH2:21][CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]5[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=5)=[CH:17][CH:18]=4)[CH:13]=3)=[O:11])=[CH:5][CH:4]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 13007N-EthylpiperidineHCID 18472361N-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 184724701-Ethyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]piperidinium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide (150mg), and to the mixture was added 1-ethylpiperidine (159 μl). The mixture was stirred at room temperature for 20 hours. Tothe reaction mixture was added ethyl acetate (100ml), and the resulting precipitate was filtered to give 1-ethyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]piperidinium chloride (Compound 34) (156mg) as colorless crystals.

Workup

  1. customTothe reaction mixture
  2. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-2ed622811da64a9995b654bd08592050
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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