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

HRID 1450059Notes

Reaction equation

HRID 1450059 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][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]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:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]1)[CH:3]=[CH:4]2)[CH3:13]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 10660349Ethyl 8-chloro-1-ethyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 19691231Ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (279 mg, 1.0 mmol), the product of Step 3 of Example 62, was dissolved in 5 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 2 mL (2.0 mmol) of N-methylpiperazine and the stirred reaction mixture was heated at 85° C. for 2.5 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 50 mL of methylene chloride and the methylene chloride solution was washed with 50 mL of 5% aqueous sodium bicarbonate solution. The aqueous layer was extracted with 3×50 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 343 mg of the title compound, m.p. 94°-96° C.; MS DCI-NH3 : 344 (M+H)+.

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 50 mL of methylene chloride
  6. washthe methylene chloride solution was washed with 50 mL of 5% aqueous sodium bicarbonate solution
  7. extractionThe aqueous layer was extracted with 3×50 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-6722b15cd94c4a2c8e84ee7ea0ae4a76
Source dataset
uspto-grants-1997_02
Patent number
US05599816

Reaction notes

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