O.O.[N+:3]([C:6]1[CH:13]=[CH:12][C:9]([O:10][Na])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19]Cl)[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C(C)=CC=CC=1>[CH2:15]([N:17]([CH2:21][CH2:22][O:10][C:9]1[CH:12]=[CH:13][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1)[CH2:18][CH3:19])[CH3:16]4-Nitrophenoxy sodium dihydrate (29.39 g), 2-(diethylamino)ethylchloride hydrochloride (25.60 g), potassium carbonate (30.17 g) and water (60 ml) were added into xylene (100 ml) and the mixture was heat-refluxed for 2 hours while mixing and continuously removing water by azeotropic distillation. After reaction, insolubles were removed by filtration. Filtrate was added with ethyl acetate (100 ml) and extracted 3 times with 1N HCl (100 ml). Aqueous layer was adjusted to pH 10 with 1N sodium hydroxide and oily substance separated was extracted 3 times with ethyl acetate (100 ml). Ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated to obtain N,N-diethyl-2-(4-nitrophenoxy)ethylamine (28.19 g) as color-less oily substance.
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