2-Methylpiperazine → HCID 14700559, compound

HRID 1084352Notes

Reaction equation

HRID 1084352 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][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1.O.[OH-].[K+]>[F:21][C:3]1[C:2]([N:27]2[CH2:26][CH2:25][NH:24][CH:23]([CH3:22])[CH2:28]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Participants

6

Reactant 2

HCID 660572-MethylpiperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 14700559HCID 14700559, compoundYield 63.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 3.5 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 4.6 g of 2-methylpiperazine in 40 cm3 of pyridine is heated at a temperature close to 115° C., with stirring, for 13 hours. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at 60° C. The residue is twice taken up with 30 cm3 of ethanol and concentrated under reduced pressure under the above conditions. The solid obtained is taken up in 60 cm3 of water and 10 cm3 of 30% aqueous potassium hydroxide solution. The aqueous phase is washed with twice 100 cm3 of trichloromethane, 10.28 g of methanesulphonic acid are added and the aqueous phase is again washed with twice 100 cm3 of trichloromethane. 10 cm3 of 30% aqueous potassium hydroxide solution are added. The precipitate formed is drained and washed with 3 times 10 cm3 of water and twice 10 cm3 of ethanol. 2.7 g of 7-fluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 360°-363° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 115° C.
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at 60° C
  4. concentrationconcentrated under reduced pressure under the above conditions
  5. customThe solid obtained
  6. washThe aqueous phase is washed with twice 100 cm3 of trichloromethane, 10.28 g of methanesulphonic acid
  7. additionare added
  8. washthe aqueous phase is again washed with twice 100 cm3 of trichloromethane
  9. addition10 cm3 of 30% aqueous potassium hydroxide solution are added
  10. customThe precipitate formed
  11. washwashed with 3 times 10 cm3 of water and twice 10 cm3 of ethanol

Sources & evidence

ORD record
ord-3814fbe0521f4a28b6cd9ee4e5de97a6
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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