Reaktion #308389

Reaktionsgleichung

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid chloride

N-Aminopiperidine

triethylamine

→

title compound

5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas -cooled to 0° C.
2. 2
   SonstigeThe resulting reaction mixture
3. 3
   WaschenThe reaction mixture was washed with water
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated to dryness in a rotavapor
7. 7
   SonstigeThe resulting crude solid was crystallised from ethanol
8. 8
   SonstigeThe crystallised solid was removed via filtration
9. 9
   Einengenthe mother liquors were concentrated
10. 10
    Sonstigeto yield a second fraction of crystallised product
11. 11
    Sonstigeto give

Vorschrift

N-Aminopiperidine (0.6 mL, 5.6 mmol) and triethylamine (4 mL) were dissolved in methylene chloride (25 mL) under nitrogen atmosphere. The resulting mixture was -cooled to 0° C. and a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid chloride in methylene chloride (15 mL) was added drop wise. The resulting reaction mixture was stirred at room temperature (approximately 25° C.) overnight. The reaction mixture was washed with water, followed by a saturated aqueous solution of sodium bicarbonate, again with water, dried over sodium sulfate, filtered and evaporated to dryness in a rotavapor. The resulting crude solid was crystallised from ethanol. The crystallised solid was removed via filtration and the mother liquors were concentrated to yield a second fraction of crystallised product. The two fractions were combined to give a total amount of 1.7 g (57% of theoretical yield) of the title compound having a melting point of 183-186° C.

Quelle