7-(4-Benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2351916Notes

Reaction equation

HRID 2351916 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[CH:16][C:15]=2[F:32])[CH2:10][CH:9]1[CH3:33])C1C=CC=CC=1>[Pd].C(O)(=O)C>[CH3:33][CH:9]1[NH:8][CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[CH:16][C:15]=2[F:32])[CH2:10]1

Participants

4

Reactant 1

HCID 156224977-(4-Benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 140525871-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 66.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 7-(4-benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.30 g) are added acetic acid (10 ml) and 10% Pd-C (50 mg), and the mixture is subjected to catalytic reduction at 70° C. under atmospheric pressure for one hour. After the catalytic reduction, the reaction mixture is cooled and the catalyst is removed by filtration. The filtrate is concentrated, and to the residue is added water, and the mixture is adjusted to about pH 7.5 with sodium hydrogen carbonate, and then is extracted with dichloromethane. The dichloromethane is distilled off, and to the residue is added diethyl ether, and the resulting precipitates are separated by filtration and recrystallized from ethanol to give 7-(3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.16 g), as pale yellow powder, m.p. 206°-208° C.

Workup

  1. temperatureAfter the catalytic reduction, the reaction mixture is cooled
  2. customthe catalyst is removed by filtration
  3. concentrationThe filtrate is concentrated
  4. additionto the residue is added water
  5. extractionis extracted with dichloromethane
  6. distillationThe dichloromethane is distilled off
  7. additionto the residue is added diethyl ether
  8. customthe resulting precipitates
  9. customare separated by filtration
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4d258fda736645ea9621bab83044e595
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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