Hydrochloric Acid → 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[(3-methoxycarbonylpropyl)-carbamoyl]-piperazin-1-yl}-quinoline-3-carboxylic acid

HRID 637928Notes

Reaction equation

HRID 637928 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.[N:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:26]=[O:27].Cl>[OH-].[Na+].O.O1CCOCC1>[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]([C:26](=[O:27])[NH:25][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[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 3

HCID 313Hydrochloric AcidHCID 2764CiprofloxacinHCID 2759393Methyl 4-isocyanatobutanoate

Product 1

HCID 133402111-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[(3-methoxycarbonylpropyl)-carbamoyl]-piperazin-1-yl}-quinoline-3-carboxylic acidYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

6.6 g (0.02 mol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid are dissolved in a solution of 0.4 g of sodium hydroxide in 40 ml of water, and a solution of 3.2 g (0.022 mol) of methyl 4-isocyanato-butyrate in 12 ml of dioxane is added, while cooling with ice. Thereafter, stirring is continued for 2 hours at room temperature, the pH is adjusted to 5 with 2N hydrochloric acid and the precipitate is filtered off under suction and recrystallised from methanol. 6 g (63% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[(3-methoxycarbonylpropyl)-carbamoyl]-piperazin-1-yl}-quinoline-3-carboxylic acid of melting point 198°-200° C. are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. filtrationthe precipitate is filtered off under suction
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-c553ee97ffc64e9a8cd039de1d3ab2c3
Source dataset
uspto-grants-1985_12
Patent number
US04559341

Reaction notes

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