Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Phenylpiperazine | HCID 250673 | — |
| Reactant | 7,8-Difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid | HCID 14853343 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 53712035 | HCID 53712035 | 68.3% |
Reaction Steps
A suspension of 7,8-difluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (2 g) and (RS)-2-phenylpiperazine (2.1 g) in dimethyl sulphoxide (30 cc) is heated with stirring for 15 minutes to approximately 50° C. After cooling to approximately 20° C., the reaction mixture is poured into water (100 cc) and treated with acetic acid (1.2 cc). The insoluble matter is drained, washed with water (3×10 cc) and recrystallized in dimethylformamide (80 cc). (RS)-7-Fluoro-1-methoxy-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (2 g) is obtained in the form of a yellow solid, decomposing at 284° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05053509 |
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| Source dataset | uspto-grants-1991_10 |
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| ORD ID | ord-cfbe001748004234ba70b60613066247 |
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| Source note | uspto-grants-1991_10 |
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