Isopropanol → Levofloxacin

HRID 1866746Notes

Reaction equation

HRID 1866746 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.CC(O)C>CCCCCCC>[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 76.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Conditions

Temperature
80 °C

Procedure

5 g (17.79 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 6.8 mL (0.06 mole) of N-methyl piperazine. The reaction mixture was heated to reflux for 40 minutes until completion of the reaction. The mixture was then cooled to 80° C. IPA (10 mL) and n-heptane (10 mL) were added at this temperature. The solid was filtrated under vacuum and rinsed with n-heptane. The mother liquor also gave a precipitate after addition of n-heptane. Both precipitates were filtrated under vacuum and dried overnight to yield 4.9 g (76%) levofloxacin.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 40 minutes until completion of the reaction
  3. filtrationThe solid was filtrated under vacuum
  4. washrinsed with n-heptane
  5. customThe mother liquor also gave a precipitate
  6. filtrationBoth precipitates were filtrated under vacuum
  7. customdried overnight

Sources & evidence

ORD record
ord-2704d4c9cba740c9913ea4ad96eac64c
Source dataset
uspto-grants-2009_12
Patent number
US07629458B2

Reaction notes

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