Réaction #78937

Équation de réaction

potassium carbonate

methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-piperidin-3-ylmethyl ester

1-(2-methoxy-phenyl)-piperazine

→

desired compound

Rendement 54.8%

1-{1-[1-(4-Choro-phenyl)-cyclopropylmethyl]-piperidin-3ylmethyl}-4-(2-methoxy-phenyl)-piperazine

Rendement 54.8%

Solvants

water

acetonitrile

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was refluxed overnight
2. 2
   Extractionextracted with EtOAc (3×50 mL)
3. 3
   SéchageThe combined organic layers were dried over sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   Autreto yield a crude oil
6. 6
   AutreThe resulting residue was purified by silica gel chromatography (96:4 DCM: 2M NH3 in EtOH)

Mode opératoire

To a solution of methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-piperidin-3-ylmethyl ester (2.94 g, 8.20 mmol) in acetonitrile (40.0 mL) at room temperature was added 1-(2-methoxy-phenyl)-piperazine (1.58 g, 8.20 mmol) followed by potassium carbonate (13.35 g, 41.0 mmol). The reaction mixture was refluxed overnight. After cooling down to room temperature the reaction mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to yield a crude oil. The resulting residue was purified by silica gel chromatography (96:4 DCM: 2M NH3 in EtOH) to obtain the desired compound as an oil (2.04 g). 13C NMR (100 MHz, CDCl3) δ152.5, 143.9, 141.8, 131.5, 130.4, 128.2, 123.1, 121.3, 118.4, 111.5, 67.8, 63.0, 59.5, 55.6, 55.2, 54.2, 51.0, 33.5, 29.8, 25.2, 23.1, 13.4, 13.1.

Source