Hydrochloric Acid → 1-Ethyl-8-(3-methyl-1-piperazinyl)-4h-quinolizin-4-one-3-carboxylic acid hydrochloride

HRID 1852Notes

Reaction equation

HRID 1852 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:21]([O:23]CC)=[O:22])[C:6](=[O:20])[N:7]2[C:12]=1[CH:11]=[C:10]([N:13]1[CH2:18][CH2:17][NH:16][CH:15]([CH3:19])[CH2:14]1)[CH:9]=[CH:8]2)[CH3:2].[OH-].[Na+].[ClH:28]>C1COCC1>[ClH:28].[CH2:1]([C:3]1[CH:4]=[C:5]([C:21]([OH:23])=[O:22])[C:6](=[O:20])[N:7]2[C:12]=1[CH:11]=[C:10]([N:13]1[CH2:18][CH2:17][NH:16][CH:15]([CH3:19])[CH2:14]1)[CH:9]=[CH:8]2)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19691415Ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate

Product 1

HCID 881513891-Ethyl-8-(3-methyl-1-piperazinyl)-4h-quinolizin-4-one-3-carboxylic acid hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 0.686 g (2 mmol) of ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 8 mL of THF was added 8.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture was heated, with stirring, at 65° C. for 3 hours. The THF was removed from the reaction mixture by distillation during the reaction. The concentrated reaction mixture was cooled to ambient temperature and adjusted to pH 1-2 with 16 mL of 1N aqueous hydrochloric acid solution. The aqueous solution was concentrated in vacuo to remove the water and the residue was suspended in 10 mL of water. The solid was collected by filtration and dried in vacuo to afford the 385 mg (55% yield) of the title compound, m.p.>295° C.; MS DCI-NH3 : 316 (M-Cl)+ ; IR (KBr): 3420 (OH), 1720 (C=O) cm-1 ; 1H NMR (TFA) d 1.50 (t, 3H, J=7.5 Hz), 1.70 (d, 3H, J=6 Hz), 3.00 (q, 2H, J=7.5 Hz), 3.70-4.10 (m, 6H), 4.55 (m, 1H), 4.60 (m, 1H), 7.40 (d, 1H, J=3.0 Hz), 7.68 (dd, 1H, J=3.0 Hz, 8.4 Hz), 8.18 (s, 1H), 9.19 (d, 1H, J=8.4 Hz). Analysis calculated for C17H22 ClN3O3 +H2O: C, 55.21; H, 6.54; N, 11.36. Found: C, 55.19; H, 6.07; N, 11.34.

Workup

  1. temperaturethe reaction mixture was heated
  2. customThe THF was removed from the reaction mixture by distillation during the reaction
  3. customThe concentrated reaction mixture
  4. temperaturewas cooled to ambient temperature
  5. concentrationThe aqueous solution was concentrated in vacuo
  6. customto remove the water
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9473a5b4f44b4bc8b8cc65bad100e385
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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