Hydrochloric Acid → HCID 12899692, compound

HRID 1649445Notes

Reaction equation

HRID 1649445 reaction equation
[N:1]1([C:7]2[C:18]3=[C:19]4[N:14]([CH2:15][CH2:16][CH2:17]3)[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[C:11](=[O:23])[C:10]4=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].[CH2:32](Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>CO.O>[CH2:32]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:18]3=[C:19]4[N:14]([CH2:15][CH2:16][CH2:17]3)[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[C:11](=[O:23])[C:10]4=[CH:9][CH:8]=2)[CH2:2][CH2:3]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12899683HCID 12899683, compound

Product 1

HCID 12899692HCID 12899692, compoundYield 9.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.0 g of 8-(1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid was added to 20 ml of water having dissolved therein 2.0 g of potassium carbonate and the mixture was stirred at room temperature for 30 minutes. After dissolving insoluble materials completely with the addition of 3 ml of 1 N aqueous sodium hydroxide solution, 10 ml of methanol having dissolved therein 0.9 g of benzyl chloride was added dropwise to the mixture while ice-cooling. After completion of the addition, the resulitng mixture was heat-refluxed for 3 hours to form a uniform solution. The solution obtained was treated with activated carbon while hot and rendered neutral with a 10% aqueous hydrochloric acid to precipitate crystals, which were separated by filtration and washed with water. Recrystallization of the crystals thus treated from dimethylformamide gave 0.25 g of 8-(4-benzyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid having a melting point of 274° to 278° C.

Workup

  1. dissolutiondissolved
  2. dissolutionAfter dissolving insoluble materials
  3. dissolutiondissolved
  4. temperaturecooling
  5. additionAfter completion of the addition
  6. temperaturethe resulitng mixture was heat-refluxed for 3 hours
  7. customto form a uniform solution
  8. customThe solution obtained
  9. additionwas treated with activated carbon while hot and
  10. customto precipitate crystals, which
  11. customwere separated by filtration
  12. washwashed with water
  13. customRecrystallization of the crystals
  14. additionthus treated from dimethylformamide

Sources & evidence

ORD record
ord-80b6787131a544019c1ab35759fa418e
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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