Реакция #1943

ord-d1417262cbeb4dcfb27be135b8b405b2

Уравнение реакции

CCOC(=O)c1ccc2cc(Cl)ccn2c1=O
Ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate
CCOC(=O)c1ccc2cc(Cl)ccn2c1=O
product
CCOC(=O)c1ccc2cc(Cl)ccn2c1=O
Ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate
CN1CCNCC1
N-methylpiperazine
CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O
title compound
Выход 106.8%
CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O
Ethyl 8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate
Выход 106.8%

Растворители

Условия реакции

Температура
70°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe reaction mixture was then concentrated in vacuo in order
  2. 2
    Другоеto remove all of the pyridine
  3. 3
    workup.DISSOLUTIONThe dry residue (3.124 g) was dissolved in 125 mL of methylene chloride
  4. 4
    Промывкаthe methylene chloride solution was washed with 125 mL of saturated sodium chloride solution (brine)
  5. 5
    ЭкстракцияThe aqueous layer was extracted with 125 mL of methylene chloride
  6. 6
    Сушкаthe combined methylene chloride solutions were dried over anhydrous sodium sulfate
  7. 7
    Фильтрацияfiltered
  8. 8
    Концентрированиеconcentrated
  9. 9
    Другоеdried in vacuo

Методика

Ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate (755 mg, 3.0 mmol), the product of Step 3 of Example 58, was suspended in 12 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 6.0 mL (6.0 mmol) of N-methylpiperazine and the reaction mixture was heated at 70° C. for 8 hours. The reaction mixture was then concentrated in vacuo in order to remove all of the pyridine. The dry residue (3.124 g) was dissolved in 125 mL of methylene chloride and the methylene chloride solution was washed with 125 mL of saturated sodium chloride solution (brine). The aqueous layer was extracted with 125 mL of methylene chloride and the combined methylene chloride solutions were dried over anhydrous sodium sulfate, filtered and concentrated and dried in vacuo to afford 1.01 g of the title compound.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05726182uspto-grants-1998_03