Dichloromethane → 6-Fluoro-4-oxo-1-phenyl-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2290241Notes

Reaction equation

HRID 2290241 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:18]([OH:20])=[O:19])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:22].C(Cl)Cl.C([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=O)C>C(N(CC)CC)C>[C:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:22])=[C:2]([N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)[N:11]=3)[C:6](=[O:21])[C:7]([C:18]([OH:20])=[O:19])=[CH:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 837951-AcetylpiperazineHCID 137153157-Chloro-6-fluoro-4-oxo-1-phenyl-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 129011646-Fluoro-4-oxo-1-phenyl-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Alternately, the title compound is prepared as follows: To a solution of 1.6 g. of compound (III) (R1 =C2H5, R=phenyl, X=Cl) (product of 1(c) in 50 ml. of methylene chloride is added 1 ml. of triethylamine and 710 mg. of N-acetylpiperazine. After heating for 2 hours, the solvent is washed with 50 ml. of 1N HCl solution and then with water. The methylene chloride solution is dried and evaporated to dryness, yielding 2.1 g. of compound (I) ##STR14##

Workup

  1. temperatureAfter heating for 2 hours
  2. washthe solvent is washed with 50 ml
  3. dry with materialThe methylene chloride solution is dried
  4. customevaporated to dryness
  5. customyielding 2.1 g

Sources & evidence

ORD record
ord-10ee32a3626a47f5a9535154f2611a99
Source dataset
uspto-grants-1986_10
Patent number
US04616019

Reaction notes

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