1-(2-Hydroxyethyl)piperazine → HCID 479051, compound

HRID 1284506Notes

Reaction equation

HRID 1284506 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:26]4[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][OH:20])[CH2:24][CH2:25]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 483180Fluoroquinolonic acid

Product 1

HCID 479051HCID 479051, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 2.81 g of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 5.2 g of N-(2-hydroxyethyl)-piperazine in 25 ml of dimethylsulphoxide is heated at 135°-140° C. for 2 hours. The solvent is distilled off under a fine vacuum, the residue is boiled up with 20 ml of water, the mixture is left to stand overnight at room temperature and the precipitate is filtered off with suction, while cooling with ice, washed with water and dried over calcium chloride in vacuo at 80° C. 2.1 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-hydroxyethyl)-1-piperazinyl]-3-quinolinecarboxylic acid of decomposition point 237°-239° C. are obtained.

Workup

  1. temperatureis heated at 135°-140° C. for 2 hours
  2. distillationThe solvent is distilled off under a fine vacuum
  3. waitthe mixture is left
  4. filtrationthe precipitate is filtered off with suction
  5. temperaturewhile cooling with ice
  6. washwashed with water
  7. dry with materialdried over calcium chloride in vacuo at 80° C

Sources & evidence

ORD record
ord-cbcf644e3b4b4b34b329bb99b4708fc0
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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