Reacción #7543

Ecuación de reacción

5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene

3-pyrrolidinol

potassium carbonate

water

→

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinol

Rendimiento 54.2%

Disolventes

N,N-dimethylformamide

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added to the solution
2. 2
   TemperaturaAfter the reaction mixture was cooled
3. 3
   Otrothe organic layer was separated
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadoa saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONdistilled under reduced pressure
7. 7
   Otroto remove the solvent
8. 8
   OtroThe residue was purified by a column chromatography (eluent; chloroform:methanol=20:1 to 10:1)

Procedimiento

In 12 mL of N,N-dimethylformamide was dissolved 1.20 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the solution, after which the resulting mixture was stirred at 85° C. for 2.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=20:1 to 10:1) to obtain 0.78 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinol as a colorless oil.

Fuente