Triethylamine → Triethyl[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]ammonium chloride

HRID 565874Notes

Reaction equation

HRID 565874 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][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[CH2:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:29]>CN(C=O)C>[Cl-:1].[CH2:28]([N+:30]([CH2:33][CH3:34])([CH2:31][CH3:32])[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][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1)[CH3:29]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10809385N-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 10648217Triethyl[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]ammonium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide 160mg), and to the mixture was added triethylamine (180 μl). The mixture was stirred at room temperature for 14 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give triethyl[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]ammonium chloride (Compound 25) (176mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b3503caea68d489daab27601c6ee7c67
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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