Reaktion #1359217

Reaktionsgleichung

1-(4-pyridyl)piperazine

nitrophenol

3-(4-methoxy-3-fluorobenzoyl)propionic acid

DIC

→

title compound

1-(3-Fluoro-4-methoxyphenyl)-4-(4-pyridin-4-ylpiperazin-1-yl)butane-1,4-dione

Lösungsmittel

1,2-dichloropropane

triethylamine

1,2-dichloropropane

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Waschenthe polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane
3. 3
   workup.ADDITIONTo the polymer was added 1,2-dichloropropane (5 ml)
4. 4
   workup.STIRRINGThe resulting mixture was shaken at room temperature for 21 hours
5. 5
   Filtrationfiltered
6. 6
   Waschenthe polymer was carefully washed with DCM and methanol
7. 7
   EinengenThe combined filtrates were concentrated
8. 8
   Sonstigeto yield the crude product as an oil (0.38 g)
9. 9
   SonstigeCrystallization from acetonitrile (2 ml) at −20° C.

Vorschrift

To the polymeric nitrophenol (1.5 g, approx. 1 mmol) was added a solution of 3-(4-methoxy-3-fluorobenzoyl)propionic acid (1.66 g, 7.34 mmol) in a mixture of 1,2-dichloropropane (15 ml) and DMF (6 ml), followed by the addition of DIC (0.78 ml, 5.01 mmol). The mixture was shaken at room temperature for 13 hours, filtered, and the polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane. To the polymer was added 1,2-dichloropropane (5 ml), a solution of 1-(4-pyridyl)piperazine (116 mg, 0.71 mmol) in 1,2-dichloropropane (10 ml), and triethylamine (0.2 ml). The resulting mixture was shaken at room temperature for 21 hours, filtered, and the polymer was carefully washed with DCM and methanol. The combined filtrates were concentrated to yield the crude product as an oil (0.38 g). Crystallization from acetonitrile (2 ml) at −20° C. yielded 0.19 g (5.1 mmol, 72%) of the title compound as almost colourless solid.

Quelle