Reaktion #2486883

Reaktionsgleichung

1-ethynylcyclohexylamine

4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid

triethylamine

N,N-bis(2-oxo-3-oxazolidinyl)phosphoramidic chloride

→

title compound

Ausbeute 31.3%

N-(1-Ethynyl-cyclohexyl)-4-[4-(2-methoxy-phenyl)piperazin-1-yl]-2-phenyl-butyramide

Ausbeute 31.3%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water (2×100 mL)
2. 2
   Trocknendried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated to dryness in vacuo

Vorschrift

A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid (1.772 g, 5 mmole), triethylamine (1.518 g, 15 mmole), and N,N-bis(2-oxo-3-oxazolidinyl)phosphoramidic chloride (1.527 g, 6 mmole) was stirred in methylene chloride (80 mL) under exclusion of moisture at ambient temperature for 30 minutes, after which 1-ethynylcyclohexylamine (0.668 g, 6 mmole) was added at once at 0° C. The reaction mixture was stirred at room temperature overnight, washed with water (2×100 mL), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Chromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether/hexane gave 0.72 g of the title compound as the 0.12 methylene chloride solvate, m.p. 127°-9° C.

Quelle