Reaktion #830216

Reaktionsgleichung

diphenylphosphoryl azide

1-(3,4,5-trimethoxybenzoyl)piperazine

(E)-3-phenyl-3-(4-pyridyl)acrylic acid

triethylamine

→

title compound

Ausbeute 86.4%

1-[(E)-3-Phenyl-3-(4-pyridyl)acryloyl]-4-(3,4,5-trimethoxybenzoyl)piperazine

Ausbeute 86.4%

Lösungsmittel

methylene chloride

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenIt was then washed with a 5% w/v aqueous solution of sodium bicarbonate
2. 2
   Trocknenthe organic phase was dried over anhydrous sodium sulfate
3. 3
   SonstigeThe solvent was then removed by distillation under reduced pressure
4. 4
   Sonstigethe oily residue (0.686 g) was purified by silica gel flash chromatography

Vorschrift

1 ml of a methylene chloride solution containing 0.330 g of diphenylphosphoryl azide and then 0.280 g of 1-(3,4,5-trimethoxybenzoyl)piperazine were added to 5 ml of a methylene chloride solution containing both 0.224 g of (E)-3-phenyl-3-(4-pyridyl)acrylic acid (prepared as described in Preparation 3) and 0.28 ml of triethylamine. The mixture was then stirred for 4 hours at room temperature, after which the reaction solution was diluted with 20 ml of methylene chloride. It was then washed with a 5% w/v aqueous solution of sodium bicarbonate, followed by a saturated aqueous solution of sodium chloride, and the organic phase was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the oily residue (0.686 g) was purified by silica gel flash chromatography. 0.419 g of the title compound was obtained as a white powder from the fractions eluted with mixtures of methylene chloride and methanol ranging from 100:2 to 100:3 by volume.

Quelle