Ciprofloxacin → HCID 13337926, compound

HRID 1284523Notes

Reaction equation

HRID 1284523 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.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)CC)C.[I-].[K+]>CN(C)C=O.O>[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]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[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

7

Reactant 4

HCID 2764CiprofloxacinHCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 13337926HCID 13337926, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.3 g (0.01 mol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid in 50 ml of dimethylformamide are heated at 90° C. with 2.5 g (0.015 mole) of ethyl bromoacetate, 1.2 g (0.02 mole) of triethylamine and 2.5 g of potassium iodide for 5 hours. The reaction mixture is poured into 30 ml of water and the precipitate is filtered off with suction, washed with water and recrystallized from methanol. 2.5 g of 1-cyclopropyl-6-fluoro-7-[4-(ethoxycarbonylmethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 192° to 194° C. are obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed with water
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-864e331b9ddc4017af38532f4a0b1951
Source dataset
uspto-grants-1986_01
Patent number
US04563448

Reaction notes

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