تفاعل #81515
ord-99859e59df4e4d4a891b01fc663e59ef
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1درجة الحرارةheated
- 2درجة الحرارةto reflux for 5 hours
- 3استخلاصextracted with ethyl acetate (3×100 mL)
- 4تجفيفThe combined extracts were dried over anhydrous magnesium sulfate
- 5ترشيحfiltered
- 6تركيزconcentrated at reduced pressure
- 7أخرىThe crude ester thus obtained
- 8أخرىwas purified by chromato-graphy on silica gel eluting with 10% methanol/chloroform
- 9أخرىThe material thus obtained
- 10درجة الحرارةto reflux for 1 hour
- 11درجة الحرارةThe reaction was then cooled to room temperature
- 12تركيزconcentrated at reduced pressure
- 13أخرىThe residue was triturated with tetrahydrofuran
- 14ترشيحthe solid collected by filtration
- 15أخرىcrystallized from isopropanol
الإجراء التجريبي
A solution of N-Benzyl-3-acetyl-3-(4-chlorobenzyl)-piperidine (492 mg, 1.44 mmol) and dimethyl oxalate (201 mg, 1.7 mmol) in dimethoxyethane (20 mL) was treated with sodium hydride (140 mg of a 60% dispersion in mineral oil, 3.4 mmol) and heated to reflux for 5 hours. The reaction was then cooled to room temperature, poured into saturated sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The crude ester thus obtained was purified by chromato-graphy on silica gel eluting with 10% methanol/chloroform. The material thus obtained was dissolved in tetrahydrofuran (5 mL) and 3N HCl (20 mL) and heated to reflux for 1 hour. The reaction was then cooled to room temperature, and concentrated at reduced pressure. The residue was triturated with tetrahydrofuran and the solid collected by filtration and crystallized from isopropanol to give 35 mg of the title compound. mp. 160°-165° C.