تفاعل #1605838

معادلة التفاعل

aripiprazole

pivaloyl chloride

→

title compound

7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2-yl pivalate

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature
2. 2
   درجة الحرارةAfter a further 5 minutes the temperature was increased to 50° C. for approximately 19 hours
3. 3
   درجة الحرارةto cool to room temperature
4. 4
   أخرىThe two reaction mixtures
5. 5
   أخرىquenched with approximately methanol (5 mL)
6. 6
   أخرىThe majority of the pyridine was removed in vacuo
7. 7
   أخرىthe residue partitioned between dichloromethane (30 mL) and saturated NaHCO3 solution (30 mL)
8. 8
   استخلاصThe aqueous phase was extracted with dichloromethane (2×30 mL)
9. 9
   غسيلthe combined organic extracts washed with brine (20 mL)
10. 10
    تجفيفdried over MgSO4
11. 11
    ترشيحAfter filtration
12. 12
    أخرىthe volatiles were removed (toluene and methanol/dichloromethane azeotrope)
13. 13
    أخرىthe residue purified by silica chromatography
14. 14
    غسيلeluting first with dichloromethane

الإجراء التجريبي

To a stirred solution of aripiprazole (0.1 g, 0.223 mmol) in pyridine (1 mL) at 0° C. was added pivaloyl chloride (0.055 mL, 0.446 mmol). After stirring at 0° C. for 5 minutes the reaction was allowed to warm to room temperature. After a further 5 minutes the temperature was increased to 50° C. for approximately 19 hours. The reaction was allowed to cool to room temperature. The reaction was repeated in a similar manner using of aripiprazole (1.75 g, 3.90 mmol). The two reaction mixtures were combined and quenched with approximately methanol (5 mL). The majority of the pyridine was removed in vacuo and the residue partitioned between dichloromethane (30 mL) and saturated NaHCO3 solution (30 mL). The aqueous phase was extracted with dichloromethane (2×30 mL) and the combined organic extracts washed with brine (20 mL) and dried over MgSO4. After filtration, the volatiles were removed (toluene and methanol/dichloromethane azeotrope) and the residue purified by silica chromatography eluting first with dichloromethane followed by ethyl acetate/dichloromethane/methanol (1:1:0.04) to give the title compound (1.19 g, 54%).

المصدر