2-Methylpiperazine → Ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate

HRID 1450057Notes

Reaction equation

HRID 1450057 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[C:9]([CH2:12][CH3:13])[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]2=[O:19].[CH3:20][CH:21]1[CH2:26][NH:25][CH2:24][CH2:23][NH:22]1>N1C=CC=CC=1>[CH2:12]([C:9]1[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:19])[N:5]2[C:10]=1[CH:11]=[C:2]([N:25]1[CH2:24][CH2:23][NH:22][CH:21]([CH3:20])[CH2:26]1)[CH:3]=[CH:4]2)[CH3:13]

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 10660349Ethyl 8-chloro-1-ethyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 19691415Ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylateYield 100.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (558 mg, 2.0 mmol), the product of Step 3 of Example 62, was dissolved in 10 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 600 mg (6.0 mmol) of 2-methylpiperazine and the stirred reaction mixture was heated at 65° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature and then concentrated in vacuo in order to remove all of the pyridine. The residue was dissolved in 60 mL of methylene chloride and the methylene chloride solution was washed with 60 mL of water. The aqueous layer was extracted with 2×60 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 690 mg of the title compound. The product was carried on to the next step without purification.

Workup

  1. customthe stirred reaction mixture
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated in vacuo in order
  4. customto remove all of the pyridine
  5. dissolutionThe residue was dissolved in 60 mL of methylene chloride
  6. washthe methylene chloride solution was washed with 60 mL of water
  7. extractionThe aqueous layer was extracted with 2×60 mL of methylene chloride
  8. dry with materialthe combined methylene chloride solutions were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-05d1dc0c0b204cb98b54291aee380fc8
Source dataset
uspto-grants-1997_02
Patent number
US05599816

Reaction notes

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