Piperazin-2-one → HCID 13191954, compound

HRID 434695Notes

Reaction equation

HRID 434695 reaction equation
Cl[C:2]1[C:11]2[CH2:12][CH:13]([CH3:14])[N:9]3[C:10]=2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]3)=[CH:4][C:3]=1[F:19].[O:20]=[C:21]1[CH2:26][NH:25][CH2:24][CH2:23][NH:22]1>CN(C)P(=O)(N(C)C)N(C)C>[O:20]=[C:21]1[NH:22][CH2:23][CH2:24][N:25]([C:2]2[C:11]3[CH2:12][CH:13]([CH3:14])[N:9]4[C:10]=3[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]4)=[CH:4][C:3]=2[F:19])[CH2:26]1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 13135548HCID 13135548, compound

Product 1

HCID 13191954HCID 13191954, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A mixture of 6 g of 9-chloro-8-fluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid, 8.6 g of 2-oxo-piperazine and 60 ml of hexamethylphosphoric triamide was reacted at 140°-150° C. on an oil bath for 6 hours. After completion of reaction, hexamethylphosphoric triamide was distilled off and to the residue was added ethyl acetate to form crystals, which then were collected by filtration. The crystals thus obtained were recrystallized twice each from dimethylformamide to give 2.4 g of 9-(3-oxo-1-piperazinyl)-8-fluoro-2-methyl-1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. m.p. not lower than 300° C., white rhombic crystals.

Workup

  1. customwas reacted at 140°-150° C. on an oil bath for 6 hours
  2. distillationwas distilled off and to the residue
  3. additionwas added ethyl acetate
  4. customto form crystals, which
  5. filtrationthen were collected by filtration
  6. customThe crystals thus obtained
  7. customwere recrystallized twice each from dimethylformamide

Sources & evidence

ORD record
ord-29c7e000582346049b26e4bc086952c8
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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