2-Methylpiperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-

HRID 2291275

Reaction equation

HRID 2291275 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:27]2[CH2:26][CH2:25][NH:24][CH:23]([CH3:22])[CH2:28]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 30666843-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-Yield 88.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.25 g), 2-methylpiperazine (2.0 g), and pyridine (13 ml) was heated at 105°-110° C. for 1 hour with stirring. The reaction mixture was evaporated to dryness under reduced pressure and water was added to the residue. The mixture was extracted with chloroform and the extract was dried. After evaporation of chloroform, ethanol was added to the residue. The resulting crystals were filtered and recrystallized from chloroform-ethanol to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.4 g), m.p. 251°-253° C.

Workup

  1. temperaturewas heated at 105°-110° C. for 1 hour
  2. customThe reaction mixture was evaporated to dryness under reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. customthe extract was dried
  6. customAfter evaporation of chloroform, ethanol
  7. additionwas added to the residue
  8. filtrationThe resulting crystals were filtered
  9. customrecrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-7575f8ad516d41479d5f0b19a63d9fe6
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Linked notes

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