Reaction #685002

Reaction equation

3-pyrrolidinol

potassium carbonate

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

water

→

achromatic oil

Yield 54.2%

1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol

Yield 54.2%

Solvents

N,N-dimethylformamide

ethyl acetate

Conditions

Workup

1. 1
   TemperatureAfter the reaction mixture was cooled
2. 2
   Otheran organic layer was separated
3. 3
   WashThe organic layer was successively washed with water
4. 4
   Dryinga saturated saline solution, and then dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThereafter, the solvent was distilled away under a reduced pressure
6. 6
   OtherThe residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1)

Procedure

1.20 g of 5-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 12 ml of N,N-dimethylformamide. Thereafter, 0.82 g of 3-pyrrolidinol and 1.30 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 85° C. for 2.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=20:1 to 10:1), so as to obtain 0.78 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinol.

Source