Ciprofloxacin → HCID 70432235, compound

HRID 1284509Notes

Reaction equation

HRID 1284509 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:25]([I:27])[CH3:26].C(N(CC)CC)C>CN(C)C=O>[IH:27].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:25][CH3:26])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 2764CiprofloxacinHCID 6340IodoethaneHCID 8471Triethylamine

Product 1

HCID 70432235HCID 70432235, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.2 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, 1.13 g of ethyl iodide, 0.73 g of triethylamine and 20 ml of N,N-dimethylformamide is heated at 70°-80° C. for 2.5 hours. The solvent is distilled off in vacuo and the residue is suspended in water. The solid is filtered off with suction, rinsed with water and pressed off on clay. 1.15 g of 1-cyclopropyl-6-fluoro-7-(4-ethyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydriodide of decomposition point 306° C. are obtained.

Workup

  1. temperatureis heated at 70°-80° C. for 2.5 hours
  2. distillationThe solvent is distilled off in vacuo
  3. filtrationThe solid is filtered off with suction
  4. washrinsed with water

Sources & evidence

ORD record
ord-c446ca23301a4207bb8cb256a371c18a
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

Loading…