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

HRID 565882Notes

Reaction equation

HRID 565882 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[CH2:37][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)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5355851-EthylazepaneHCID 18472361N-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 184722571-Ethyl-1-[4-[7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]perhydroazepinium chlorideYield 68.8%

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-ethylperhydroazepine (98mg). The mixture was stirred at room temperature for 15 hours. To the reaction mixture was added ethyl acetate (100ml), and the resulting precipitate was filtered and recrystallized from ethylacetate-methanol to give 1-ethyl-1-[4-[7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]perhydro-azepinium chloride (Compound 37) (137mg) as colorless crystals.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customrecrystallized from ethylacetate-methanol

Sources & evidence

ORD record
ord-10cc66a9fd0f4293a6b820d676cca7d4
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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