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

HRID 1387806Notes

Reaction equation

HRID 1387806 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 (3 ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (160 mg), 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) (176 mg) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-92c81db3b86c449fb691217a9dd969a2
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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