1-Methylpiperazine → N-Methylciprofloxacin

HRID 1284505Notes

Reaction equation

HRID 1284505 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 483180Fluoroquinolonic acid

Product 1

HCID 465907N-MethylciprofloxacinYield 59.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 20 g of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 28.5 g of N-methylpiperazine and 120 ml of anhydrous dimethylsulphoxide is heated at 135°-140° C. for 2.5 hours. The solvent is distilled off under a fine vacuum and the residue is suspended in about 50 ml of water. The solid is filtered off with suction, rinsed with water, dried over calcium chloride in a vacuum drying cabinet at 80° C. and recrystallized from glycol monomethyl ether. 14.5 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinolinecarboxylic acid of decomposition point 248°-250° C. are obtained.

Workup

  1. temperatureis heated at 135°-140° C. for 2.5 hours
  2. distillationThe solvent is distilled off under a fine vacuum
  3. filtrationThe solid is filtered off with suction
  4. washrinsed with water
  5. dry with materialdried over calcium chloride in a vacuum
  6. customdrying cabinet at 80° C.
  7. customrecrystallized from glycol monomethyl ether

Sources & evidence

ORD record
ord-1724f4b515014d9f893eb661a686b58d
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

Loading…