Hydrochloric Acid → 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

HRID 1788983Notes

Reaction equation

HRID 1788983 reaction equation
Cl.[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:23])=[C:12]([N:16]4[CH2:21][CH2:20][N:19]([OH:22])[CH2:18][CH2:17]4)[C:13]=3[F:15])[C:8](=[O:24])[C:7]([C:25]([OH:27])=[O:26])=[CH:6]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl>O>[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:23])=[C:12]([N:16]4[CH2:17][CH2:18][N:19]([OH:22])[CH2:20][CH2:21]4)[C:13]=3[F:15])[C:8](=[O:24])[C:7]([C:25]([OH:27])=[O:26])=[CH:6]2)[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 30658513-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6,8-difluoro-7-(4-hydroxy-1-piperazinyl)-4-oxo-, monohydrochloride

Product 1

HCID 30658521-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidYield 62.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid hydrochloride (1.00 g) as prepared above is suspended in water (40 ml). To the suspension is added triethylamine and then the pH of the solution is adjusted to 7.0 with 1N HCl. The resulting precipitate is filtered and washed with water to yield crude 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid (0.85 g) as a colorless powder. The crude product is recrystallized from a mixture of dimethylformamide and water to afford 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid (0.57 g) as pale yellow prisms. The melting point, infrared and nuclear magnetic resonance spectra of this product are consistent with those of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid obtained in Example 5.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with water
  3. customto yield crude 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid (0.85 g) as a colorless powder
  4. customThe crude product is recrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-1baa66e35b14439c886bec969de02497
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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