Reaktion #1095081

Reaktionsgleichung

hydrochloric acid

5-[2-(3-chloropropyloxy)ethyl]benzo[b]-thiophene

diethylamine

water

→

N-[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-N,N-diethylamine

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe aqueous layer is separated
3. 3
   workup.ADDITIONEthyl acetate is added to the aqueous layer
4. 4
   Sonstigethe organic layer is separated
5. 5
   WaschenThe organic layer is washed with water and saturated aqueous solution of sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
8. 8
   Sonstigethe residue is purified by column chromatography (eluent: chloroform:methanol=10:1 to 4:1)

Vorschrift

In 6 mL of N,N-dimethylformamide is dissolved 0.80 g of 5-[2-(3-chloropropyloxy)ethyl]benzo[b]-thiophene, to which is added 3.2 mL of diethylamine. The mixture is stirred in an ampoule at 100° C. for 10 hours. After cooling, the reaction mixture is introduced into a mixture of water and ethyl acetate, pH is adjusted to 1.0 with 6 mol/L hydrochloric acid, and the aqueous layer is separated. Ethyl acetate is added to the aqueous layer, pH is adjusted to 10.0 with 5 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride 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 to 4:1). Thus, 0.48 g of N-[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-N,N-diethylamine is obtained as an oily product.

Quelle