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

HRID 1788981Notes

Reaction equation

HRID 1788981 reaction equation
Cl.Cl.[OH:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[CH:17]1([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:32])=[C:27](F)[C:28]=3[F:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21]2)[CH2:19][CH2:18]1>CS(C)=O>[CH:17]1([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:32])=[C:27]([N:7]4[CH2:8][CH2:9][N:4]([OH:3])[CH2:5][CH2:6]4)[C:28]=3[F:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 12463394Piperazin-1-ol dihydrochloride

Product 1

HCID 30658521-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidYield 71.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

1-Hydroxypiperazine dihydrochloride (4.64 g), triethylamine (8.9 g) and dimethylsulfoxide (25 ml) are added to 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (5.0 g), which is prepared according to the procidures described in Japanese Patent First Publication No. 212474/1984, and the mixture is stirred with heating at 130° C. for 45 minutes. After cooling of the mixture to room temperature, the resulting crystals are filtered. To the crystals is added water (20 ml) and the mixture is stirred at 50° C. for 1 hour. The insoluble substance is filtered and 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 (4.6 g) as pale yellow prisms, m.p. 223°-227° C. (decomposed with foaming).

Workup

  1. customis prepared
  2. temperatureAfter cooling of the mixture to room temperature
  3. filtrationthe resulting crystals are filtered
  4. additionTo the crystals is added water (20 ml)
  5. stirringthe mixture is stirred at 50° C. for 1 hour
  6. filtrationThe insoluble substance is filtered
  7. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-a8128302981244928c282a1627e02429
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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