7-(4-Benzyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 7-(1-Piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
Reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[CH:16][C:15]=2[F:32])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[N:11]1([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[CH:16][C:15]=2[F:32])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 7-(4-benzyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4 -dihydro-4-oxoquinoline-3-carboxylic acid (84 mg) are added acetic acid (3 ml) and 10% Pd-C (10 mg), and the mixture is subjected to catalytic reduction at 70° C. for one hour. After the catalytic reduction, the reaction mixture is cooled and the catalyst is filtered off. The filtrate is concentrated, and to the residue is added aqueous sodium hydrogen carbonate, and the resulting precipitates are separated by filtration to give 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (45 mg), as white crystals, m.p. 291°-295° C. (decomp.).
Workup
- temperatureAfter the catalytic reduction, the reaction mixture is cooled
- filtrationthe catalyst is filtered off
- concentrationThe filtrate is concentrated
- additionto the residue is added aqueous sodium hydrogen carbonate
- customthe resulting precipitates
- customare separated by filtration
Sources & evidence
- ORD record
- ord-04fc42fc1d1b40b7ba932476ba51b922
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04880806
Reaction notes
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