Ethyl Acetate → HCID 18472240, compound

HRID 565884Notes

Reaction equation

HRID 565884 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[CH2:38][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)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 144619Octahydroazocine, 1-ethyl-HCID 18472361N-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 18472240HCID 18472240, compoundYield 69.4%

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-ethylperhydroazocine (109mg). The mixture was stirred at room temperature for 14 hours. To the reaction mixture was added ethyl acetate (100ml), and the resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give 1-ethyl-1-[4-[7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxamido]benzyl]perhydro-azocinium chloride (Compound 39) (142mg) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-769d92f7daae4c36af3d448892a48a64
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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