Water → Pefloxacin

HRID 729056Notes

Reaction equation

HRID 729056 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Cl)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[Si]([N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 194347814-(t-Butyldimethylsilyl)-1-methyl piperazine

Product 1

HCID 51081PefloxacinYield 312%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.5 g (1.85 mmol) of 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (II, R1 : ethyl; X: chloro) and 1.07 g (0.50 mmol) of 4-(t-butyldimethylsilyl)-1-methyl piperazine (III, R2, R3 and R4 : methyl; R5 : t-butyl) are added to 100 ml of acetonitrile and then heated with stirring. A solution of 1.60 g (0.50 mmol) of tetrabutyl ammonium fluoride trihydrate in 5 ml of acetonitrile is added dropwise to the reaction mixture. After heating with stirring for 3 hours,the solvent is stripped off and water is added thereto to give a solid. After filtering and drying, 0.52 g (85% yield) of a solid compound is afforded.

Workup

  1. temperatureheated
  2. temperatureAfter heating
  3. stirringwith stirring for 3 hours
  4. customto give a solid
  5. filtrationAfter filtering
  6. customdrying

Sources & evidence

ORD record
ord-a5b41720e0e94620bf242dd1ee790cea
Source dataset
uspto-grants-1991_09
Patent number
US05051505

Reaction notes

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