Isopropanol → Levofloxacin

HRID 1866743Notes

Reaction equation

HRID 1866743 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O)(C)C>CS(C)=O>[CH3:10][C@@H:7]1[N:6]2[C:5]3[C:14]([C:13]([C:12]([C:17]([OH:19])=[O:18])=[CH:11]2)=[O:16])=[CH:15][C:2]([F:1])=[C:3]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)[C:4]=3[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 531671-MethylpiperazineHCID 688333Levofloxacin q-acid

Product 1

HCID 149096LevofloxacinYield 91.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

5 g (17.8 mmole) of (S)-(−)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][1,4]benzoxazine-6-carboxylic acid was put in suspension in 2.5 mL of DMSO and 4.2 mL (37.9 mmole) of N-methyl piperazine. The reaction mixture was heated to 120° C. and the suspension became soluble. After 2.5 h the reaction was completed. The mixture was then cooled to 70° C. and isopropanol (25 mL) was then added at this temperature. The reaction mixture was slurried for 1 h at ambient temperature, filtered, and dried overnight to obtain 5.86 g (91.3%) of levofloxacin.

Workup

  1. temperatureThe mixture was then cooled to 70° C.
  2. waitThe reaction mixture was slurried for 1 h at ambient temperature
  3. filtrationfiltered
  4. customdried overnight

Sources & evidence

ORD record
ord-10ae94f2f14f48479b02a558a198b295
Source dataset
uspto-grants-2009_12
Patent number
US07629458B2

Reaction notes

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