1-Methylpiperazine → Ethyl 8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate

HRID 1080189

Reaction equation

HRID 1080189 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>N1C=CC=CC=1>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]3=[O:17])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate2×

Product 1

HCID 15389003Ethyl 8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylateYield 106.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo in order
  2. customto remove all of the pyridine
  3. dissolutionThe dry residue (3.124 g) was dissolved in 125 mL of methylene chloride
  4. washthe methylene chloride solution was washed with 125 mL of saturated sodium chloride solution (brine)
  5. extractionThe aqueous layer was extracted with 125 mL of methylene chloride
  6. dry with materialthe combined methylene chloride solutions were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c6eeaf26a337465ab4705a3b17c371f0
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Linked notes

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