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

HRID 2228073Notes

Reaction equation

HRID 2228073 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-cbf2fcf887134e66ae496d12b5821cf5
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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