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ChemicalBook CAS DataBase List Diethyl-[2-(3-nitrophenoxy)ethyl]aMine
213606-47-4

Diethyl-[2-(3-nitrophenoxy)ethyl]aMine synthesis

2synthesis methods
-

Yield:213606-47-4 84%

Reaction Conditions:

with caesium carbonate in ethanol; for 12 h;Heating / reflux;

Steps:

1.1g

Diethyl-[2-(3-nitro-phenoxy)-ethyl]-amine can be synthesize by the following procedure.To a solution of 3-nitro-phenol (7.2 mmol) in anhydrous EtOH (20 mL), cesium carbonate (10.8 mmol) is added followed by (2-chloro-ethyl)-diethyl-amine hydrochloride (7.0 mmol) and the reaction mixture is refluxed for 12 h. The reaction mixture is cooled down and the solid filtered under vacuum and washed with warm EtOH. The filtrate is concentrated, dissolved in DCM (50 mL), washed with water, brine, dried over Na2SO4, and concentrated to afford 1.45 g of the title compound (84%) that is used without further purification. 1HNMR (400MHz, CDCl3) δ 7.82-8.80 (m, IH), 7.74-7.73 (no, IH), 7.43-7.38 (m, IH), 7.23-7.21 (m, IH), 4.12 (dt, J = 8.0 and 4.0 Hz, 2H), 2.91 (dt. J = 8.0 and 4.0 Hz, 2H), 2.69-2.63 (m,4H), 1.11-1.06 (m, 6H). MS (m/z) (M+l)+ 239.2.

References:

WO2007/38669,2007,A2 Location in patent:Page/Page column 171