Heptane → Levofloxacin

HRID 1866744Notes

Reaction equation

HRID 1866744 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.CCCCCCC>CC(O)COC>[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 8900HeptaneHCID 531671-MethylpiperazineHCID 688333Levofloxacin q-acid

Product 1

HCID 149096LevofloxacinYield 77.3%

Reagents, catalysts & solvents 1

HCID 79001-Methoxy-2-propanolSolvent

Conditions

Temperature
90 °C

Procedure

3 g (10.67 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 30 mL of PGME and 4.75 mL (43 mmole) of N-methyl piperazine. The reaction mixture was heated to reflux for 23 hours until completion of the reaction. During that time, the reaction mixture became soluble. The mixture was then cooled to 90° C. and n-Heptane (10 mL) was added at this temperature. The reaction mixture was then cooled to 0° C. and the precipitation occurred around 65° C. The reaction was left at 0° C. for 3 hours, filtrated under vacuum and dried overnight to obtain 2.98 g (77.3%) of levofloxacin.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 23 hours until completion of the reaction
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. customthe precipitation
  5. customoccurred around 65° C
  6. filtrationfiltrated under vacuum
  7. customdried overnight

Sources & evidence

ORD record
ord-ac1b154497184dc0bfd8deb196e66413
Source dataset
uspto-grants-2009_12
Patent number
US07629458B2

Reaction notes

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