Hydrochloric Acid → 8-Cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)-3-quinolinecarboxylic acid

HRID 1613032Notes

Reaction equation

HRID 1613032 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:21].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.Cl>O1CCOCC1>[C:12]([C:11]1[C:2]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:3]([F:21])[CH:4]=[C:5]2[C:10]=1[N:9]([CH:14]1[CH2:16][CH2:15]1)[CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6]2=[O:20])#[N:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 153471917-Chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 197766128-Cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.5 g of the product from Example 1 and 0.42 g of piperazine are boiled in 8 ml of dioxane for 3 hours. The mixture is then concentrated in vacuo and 8 ml of water are added to the residue. The solution formed is rendered neutral with HCl and the solid which has precipitated out isolated, washed and dried.

Workup

  1. concentrationThe mixture is then concentrated in vacuo and 8 ml of water
  2. additionare added to the residue
  3. customThe solution formed
  4. customthe solid which has precipitated out
  5. customisolated
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-8d284ba38f0647b5a2f783017f1771d7
Source dataset
uspto-grants-1993_03
Patent number
US05190955

Reaction notes

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