Dabco → HCID 13565039, compound

HRID 745482Notes

Reaction equation

HRID 745482 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].[C:20]1([CH:26]2[CH2:31][NH:30][CH2:29][CH2:28][NH:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N12CCN(CC1)CC2>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:30]4[CH2:29][CH2:28][NH:27][CH:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:31]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

5

Reactant 3

HCID 9237DabcoHCID 2506732-PhenylpiperazineHCID 483180Fluoroquinolonic acid

Product 1

HCID 13565039HCID 13565039, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.8 g (0.01 mols) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.8 g (0.011 mole) of 2-phenylpiperazine and 2.2 g (0.02 mole) of 1,4-diazabicyclo[2.2.2]octane in 6 ml of dimethyl sulphoxide is heated at 140° C. for 4 hours. The solution is concentrated under high vacuum, and the residue is stirred with 20 ml of water and the pH is adjusted to 7 with 2N hydrochloric acid. The precipitate is filtered off with suction, washed with water and methanol, and boiled in 30 ml of methanol. 1.3 g (32% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-phenyl-1-piperazinyl)-3-quinolinecarboxylic acid of melting point 218°-220° (with decomposition) is obtained (recrystallized from glycol monomethyl ether).

Workup

  1. concentrationThe solution is concentrated under high vacuum
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with water and methanol

Sources & evidence

ORD record
ord-25fcb9ce44e5406a8f0677d0977da05c
Source dataset
uspto-grants-1986_07
Patent number
US04599334

Reaction notes

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