Hydrochloric Acid → HCID 13850788, compound

HRID 1382211Notes

Reaction equation

HRID 1382211 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.Cl[CH2:26][CH:27]1[CH2:29][CH2:28]1.[I-].[K+].Cl>CN(C)C=O.O.C(N(CC)CC)C>[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][CH:27]5[CH2:29][CH2:28]5)[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2764CiprofloxacinHCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropane

Product 1

HCID 13850788HCID 13850788, compoundYield 15.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3.3 g (10 mmol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are heated at 90° in 50 ml of dimethylformamide with 1.8 g (20 mmol) of chloromethylcyclopropane, 3.3 g (20 mmol) of potassium iodide and 2.1 g of triethylamine for 5 hours. The solution is poured into 40 ml of water, the pH is brought to 5 with 2N hydrochloric acid and the precipitate is filtered off with suction and recrystallized from methanol. 0.6 g of 1-cyclopropyl-7-(4-cyclopropylmethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 279°-282° (with decomposition) is obtained.

Workup

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

Sources & evidence

ORD record
ord-612a8e0168aa42e4be4afbd7f8f29d42
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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