Réaction #685003

ord-cee20684df424265b31bbaca6c319465

Équation de réaction

CCN(CC)CC
triethylamine
CC(=O)Cl
acetyl chloride
NC1CCN(CCCOCCc2ccc3sccc3c2)C1
1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinamine
O
water
CC(=O)NC1CCN(CCCOCCc2ccc3sccc3c2)C1
yellow oil
CC(=O)NC1CCN(CCCOCCc2ccc3sccc3c2)C1
N-(1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinyl)acetamide

Conditions de réaction

Température
-60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrean organic layer was then separated
  2. 2
    LavageThe organic layer was washed with a saturated saline solution
  3. 3
    Séchagedried over anhydrous magnesium sulfate
  4. 4
    workup.DISTILLATIONThe solvent was then distilled away under a reduced pressure
  5. 5
    AutreThe residue was purified by column chromatography (eluent; chloroform:methanol=50:1 to 10:1)

Mode opératoire

0.50 g of 1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinamine was dissolved in 5 ml of methylene chloride. The obtained solution was cooled to −60° C. Thereafter, 0.27 ml of triethylamine and 0.14 ml of acetyl chloride were added thereto, and the obtained mixture was stirred at a room temperature for 1 hour. Thereafter, water and ethyl acetate were added to the reaction mixture, and an organic layer was then separated. The organic layer was washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent was then distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=50:1 to 10:1), so as to obtain 0.55 g of a yellow oil product, N-(1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-pyrrolidinyl)acetamide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07897594B2uspto-grants-2011_03