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

HRID 1649453Notes

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]

Participants

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

customAfter completion of the reaction
customthe solvent was removed by distillation under reduced pressure
washthe residue was washed with water
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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