Acetic Acid → HCID 15571789, compound

HRID 1649450Notes

Reaction equation

HRID 1649450 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[Br:20].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CN(C)P(=O)(N(C)C)N(C)C.C(O)(=O)C>O>[BrH:20].[N:21]1([C:3]2[C:4]3=[C:13]4[N:8]([CH:7]([CH3:19])[CH2:6][CH2:5]3)[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11](=[O:15])[C:12]4=[CH:14][C:2]=2[F:1])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4837PiperazineHCID 12679HexamethylphosphoramideHCID 13472993HCID 13472993, compound

Product 1

HCID 15571789HCID 15571789, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 3.8 g of anhydrous piperazine and 30 ml of hexamethylphosphoric triamide was heated at 150° to 160° C. on a water bath for 5 hours in an argon stream. After completion of the reaction the solvent was removed under reduced pressure and 20 ml of ethyl acetate was added to the residue. The crystals precipitated were collected by filtration. The crystals thus-obtained were dissolved in 300 ml of water and the solution was adjusted to a pH of 4 with acetic acid. After adding activated carbon to the solution and filtering, the filtrate was concentrated under reduced pressure. Recrystallization of the crude crystals precipitated from isopropanol-water (2:1 by volume) gave 2.7 g of 8-(1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-benzo[ij]quinolizine-2-carboxylic acid hydrobromide as rhombic crystals having a melting point of 300° C. or more.

Workup

  1. temperaturewas heated at 150° to 160° C. on a water bath for 5 hours in an argon stream
  2. customAfter completion of the reaction the solvent
  3. customwas removed under reduced pressure and 20 ml of ethyl acetate
  4. additionwas added to the residue
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. customThe crystals thus-obtained
  8. additionAfter adding activated carbon to the solution
  9. filtrationfiltering
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customRecrystallization of the crude crystals
  12. customprecipitated from isopropanol-water (2:1 by volume)

Sources & evidence

ORD record
ord-98f501f2df9f49369dac8547b55bd4ef
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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