7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acid

HRID 248464Notes

Reaction equation

HRID 248464 reaction equation
[O:1]([CH2:8][CH:9]1[NH:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:16]1[CH:25]=[C:24]2[C:19]([C:20](=[O:31])[C:21]([C:28]([OH:30])=[O:29])=[CH:22][N:23]2[CH2:26][CH3:27])=[CH:18][C:17]=1[F:32]>N1C=CC=CC=1>[CH2:26]([N:23]1[C:24]2[C:19](=[CH:18][C:17]([F:32])=[C:16]([N:11]3[CH2:12][CH2:13][NH:14][CH:9]([CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:10]3)[CH:25]=2)[C:20](=[O:31])[C:21]([C:28]([OH:30])=[O:29])=[CH:22]1)[CH3:27]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197636043-Phenoxymethylpiperazine

Product 1

HCID 148393551-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acidYield 46.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2 g of 3-phenoxymethylpiperazine and 701 mg of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10 ml of pyridine was heated under argon in a pressure bottle at 130° C. for 18 hours. The solvents were removed and the residue chromatographed on silica gel, eluting with chloroform:methanol (9:1). The appropriate fractions were combined, evaporated, triturated with methanol and ether, then dried, giving 519 mg of the desired compound, mp 198°-200° C.

Workup

  1. customThe solvents were removed
  2. customthe residue chromatographed on silica gel
  3. washeluting with chloroform:methanol (9:1)
  4. customevaporated
  5. customtriturated with methanol and ether
  6. customdried

Sources & evidence

ORD record
ord-b8fee752830b4340872bb1e8ffe1ea49
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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