Isopropyl iodide → 1-Cyclopropyl-6,8-difluoro-7-(4-isopropylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydriodide

HRID 1710184Notes

Reaction equation

HRID 1710184 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[C:12]=3[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.[CH:26]([I:29])([CH3:28])[CH3:27].C(N(CC)CC)C>CN(C)C=O>[IH:29].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:16][CH2:17][N:18]([CH:26]([CH3:28])[CH3:27])[CH2:19][CH2:20]4)[C:12]=3[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 8471TriethylamineHCID 1228488-Fluorociprofloxacin

Product 1

HCID 133655571-Cyclopropyl-6,8-difluoro-7-(4-isopropylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydriodideYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.5 g (0.01 mol) of 1-cyclopropyl-6,8-difluoro-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 3.4 g (0.02 mol) of isopropyl iodide and 2.1 (0.02 mol) of triethylamine in 50 ml of dimethylformamide is heated to 80° C. in the course of 6 hours. After the solvent has been evaporated off, the residue is stirred with 30 ml of water and is then filtered off under suction, washed with water and recrystallised from methanol. 2.3 g of 1-cyclopropyl-6,8-difluoro-7-(4-isopropylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydriodide having a decomposition temperature of 306°-308° C. are obtained.

Workup

  1. customAfter the solvent has been evaporated off
  2. filtrationis then filtered off under suction
  3. washwashed with water
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-718952340694440989e24728daf9286a
Source dataset
uspto-grants-1990_08
Patent number
US04952695

Reaction notes

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