Water → HCID 12899690, compound

HRID 1649443Notes

Reaction equation

HRID 1649443 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.[Na+].O.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[C:30]([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)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 12899683HCID 12899683, compound

Product 1

HCID 12899690HCID 12899690, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.0 g of 8-(1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid and 1.2 g of sodium hydrogen carbonate were added to 30 ml of water and the mixture was stirred at room temperature for 30 minutes. 5 ml of acetone having dissolved therein 1.0 g of benzoyl chloride was added dropwise to the mixture while ice-cooling followed by stirring at the same temperature as above for 30 minutes and then at room temperature for 1.5 hours to precipitate crystals, which were separated by filtration and washed with water. Recrystallization of the crystals thus-treated from dimethylformamide gave 2.4 g of 8-(4-benzoyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as white needles having a melting point of not lower than 300° C.

Workup

  1. temperaturecooling
  2. stirringby stirring at the same temperature as above for 30 minutes
  3. customat room temperature for 1.5 hours to precipitate crystals, which
  4. customwere separated by filtration
  5. washwashed with water
  6. customRecrystallization of the crystals
  7. additionthus-treated from dimethylformamide

Sources & evidence

ORD record
ord-917e13e727d048a1a4691420ee4c872c
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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