Hydrochloric Acid → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(4-piperidinylmethyl)-1-piperazinyl]-3-quinolinecarboxylic acid monohydrochloride

HRID 373322Notes

Reaction equation

HRID 373322 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:28])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23](C=O)[CH2:22][CH2:21]4)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:29])[C:5]([C:30]([OH:32])=[O:31])=[CH:4]1)[CH3:2].[ClH:33]>O1CCOCC1>[ClH:33].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:28])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:29])[C:5]([C:30]([OH:32])=[O:31])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 198123041-Ethyl-6-fluoro-1,4-dihydro-7-[4-[(1-formyl-4-piperidinyl)methyl]-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 678962551-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(4-piperidinylmethyl)-1-piperazinyl]-3-quinolinecarboxylic acid monohydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the N-formylquinolone from Example 18, (1.0 g, 2.25 mmol) in dioxane (20 mL) and aqueous hydrochloric acid (1N, 20 mL) was heated at 100° C. for 31/2 hours. The solvent was removed and the residue was recrystallized from methanol to give the product as a white crystalline solid (0.85 g, 85% yield).

Workup

  1. customThe solvent was removed
  2. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-6e73da833dae4705a0673eb0994987d8
Source dataset
uspto-grants-1992_11
Patent number
US05162523

Reaction notes

Loading…