Réaction #60490

Équation de réaction

water

4-[3-(4,4-diethylcyclohexyl)-4-piperazin-1-ylphenyl]morpholine

potassium carbonate

1-bromo-2-butanone

→

1-[4-[2-(4,4-diethylcyclohexyl)-4-morpholin-4-ylphenyl]piperazin-1-yl]butan-2-one

Solvants

ethyl acetate

dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureAfter air-cooling
2. 2
   LavageThe organic layer was washed with water
3. 3
   Filtrationfiltered through Celite
4. 4
   Concentrationthe filtrate was concentrated
5. 5
   AutreThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Mode opératoire

To a solution of 4-[3-(4,4-diethylcyclohexyl)-4-piperazin-1-ylphenyl]morpholine (20 mg, 0.052 mmol) produced in Example (84b) in dimethylformamide (1 mL) were added potassium carbonate (11 mg, 0.078 mmol) and 1-bromo-2-butanone (9.4 mg, 0.063 mmol), followed by stirring for 2 hours and 5 minutes at an external temperature of 80° C. After air-cooling, water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and then filtered through Celite, and the filtrate was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-[4-[2-(4,4-diethylcyclohexyl)-4-morpholin-4-ylphenyl]piperazin-1-yl]butan-2-one. This compound was dissolved in ethyl acetate, and a 4N solution of hydrogen chloride in ethyl acetate (0.020 mL, 0.080 mmol) was added. The solution was concentrated under reduced pressure, and then hexane was added to the obtained residue to produce a solid. The solid was triturated by sonication and the supernatant hexane solution was removed. The obtained solid residue was dried under reduced pressure to give 25 mg of the title compound as a white solid.

Source