Water → N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amine

HRID 1007890Notes

Reaction equation

HRID 1007890 reaction equation
[OH-].[Na+].[C:3]1([CH2:13][CH2:14][OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl.Cl[CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].O>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH2:22][O:15][CH2:14][CH2:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 13047Naphthalen-1-ethanolHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 22666300N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amineYield 96.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In a mixture of 1 mL of toluene and 3.5 ml of 50% (W/V) aqueous solution of sodium hydroxide is suspended 0.70 g of 2-(1-naphthyl)-1-ethanol, to which are added 1.00 g of N-(2-chloroethyl)-N,N-diethylamine hydrochloride and 0.14 g of tetra-n-butylammonium hydrogen sulfate. The mixture is heated under reflux for 2.5 hours. Water and toluene are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent:chloroform:methanol=10:1). Thus, 1.06 g of N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amine is obtained as an oily product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2.5 hours
  3. customthe organic layer is separated
  4. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography (eluent:chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2fe18f332ad74cbe881d18eae9764afc
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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