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Trifluoroacetylpiperazine → 8-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 1649453
Notes
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Reaction equation

HRID 1649453 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]2)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]3=[CH:4][C:3]=1[Cl:20].[F:21][C:22]([F:32])([F:31])[C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24]>CN(P(N(C)C)(N(C)C)=O)C>[F:32][C:22]([F:21])([F:31])[C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[C:13]3=[C:14]4[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]3)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]4=[CH:4][C:3]=2[Cl:20])[CH2:27][CH2:26]1)=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7172020TrifluoroacetylpiperazineHCID 155717798,9-dichloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Product 1

HCID 132695268-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidYield 50.6%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3.1 g of 8,9-dichloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 9.1 g of 1-trifluoroacetylpiperazine and 50 ml of HMPTA was heated at 160° C. for 4 hours under atmosphere of argon. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was washed with water. Recrystallization of the residue from dimethylformamide gave 2.3 g of 8-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as white rhombic crystals having a melting point of 300° C. or more.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. washthe residue was washed with water
  4. customRecrystallization of the residue from dimethylformamide

Sources & evidence

ORD record
ord-b505f1c8a1d0416998a46b8950cf7ad2
Source dataset
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04416884

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes