2,2-Dimethylpiperazine → HCID 20063307, compound

HRID 1084381Notes

Reaction equation

HRID 1084381 reaction equation
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[CH3:22][C:23]1([CH3:29])[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1.C(OCC)C>[CH3:22][C:23]1([CH3:29])[NH:24][CH2:25][CH2:26][N:27]([C:2]2[C:3]([F:21])=[CH:4][C:5]3[C:6]([CH:20]=2)=[N:7][C:8]2[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=2[CH:14]=3)[CH2:28]1

Participants

5

Reactant 2

HCID 146641862,2-DimethylpiperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 20063307HCID 20063307, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 2 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid in 7.44 g of 2,2-dimethylpiperazine and 20 cm3 of pyridine is heated at a temperature close to 115° C. for 44 hours. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 60° C. The residue is taken up in 50 cm3 of ethanol and again concentrated, under reduced pressure, under the above conditions. The solid obtained is taken up in 50 cm3 of diethyl ether, drained, washed with twice 30 cm3 of the same solvent and taken up in 120 cm3 of water and 2 g of methanesulphonic acid. A very small amount of insoluble matter is removed by filtering through diatomaceous silica. 2 cm3 of 50% aqueous potassium hydroxide solution are added to the solution obtained. The precipitate formed is drained and washed with 3 times 25 cm3 of water and a single amount of 50 cm3 of ethanol at about 50° C. 1.6 g of 8-(3,3-dimethyl-1-piperazinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 362°-365° C., solvated by 4.9% of water.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 115° C. for 44 hours
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 60° C
  4. concentrationagain concentrated, under reduced pressure, under the above conditions
  5. customThe solid obtained
  6. washwashed with twice 30 cm3 of the same solvent
  7. customA very small amount of insoluble matter is removed
  8. filtrationby filtering through diatomaceous silica
  9. addition2 cm3 of 50% aqueous potassium hydroxide solution are added to the solution
  10. customobtained
  11. customThe precipitate formed
  12. washwashed with 3 times 25 cm3 of water
  13. customat about 50° C

Sources & evidence

ORD record
ord-6a7fbada03344ad0a8e45e5d4e2f0e18
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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