Hydrochloric Acid → Oxociprofloxacin

HRID 280104Notes

Reaction equation

HRID 280104 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26].N12CCN(CC1)CC2.Cl>O.CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:23]4[CH2:24][CH2:25][NH:20][C:21](=[O:26])[CH2:22]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 231360Piperazin-2-oneHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 128242OxociprofloxacinYield 72.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

5.3 g (20 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are initially introduced into 50 ml of DMSO and heated with 2.4 g (24 mmol) of 2-piperazinone and 4.4 g (40 mmol) of 1,4-diazabicyclo[2.2.2]octane at 130° C. for 1 hour. After cooling, the suspension is adjusted to pH 5 with 2 N hydrochloric acid, 50 ml of water are added, and the precipitate is filtered off with suction, washed with water and methanol, and then boiled in 50 ml of methanol. 5 g (72% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic acid of melting point 342°-348° C. (decomposition) and purity 97% (HPLC) are isolated. Mass spectrum: m/e 345 (M+), 301 (94%, M+--CO2), 231 (M+--C 3 H4NO), 202, 44 (100%, CO2). NMR (CF3COOH)=δ1.45 and 1.7 broad (4H in the cyclopropyl radical), 3.9 and 4.0 broad (5H, N--CH in the cyclopropyl radical, N--CH2CH2 --N), 4.6 broad (2H, CO--CH2 --N), 7.85 d (1H, on C-8), 8.28 d (1H, on C-5), 9.3 s (1H, on C-2).

Workup

  1. temperatureAfter cooling
  2. additionare added
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-daaf539354f54b719cf742483e17905a
Source dataset
uspto-grants-1986_05
Patent number
US04588726

Reaction notes

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