1-Methylpiperazine → HCID 20063292, compound

HRID 1084382Notes

Reaction equation

HRID 1084382 reaction equation
Cl[C:2]1[C:3]([F:23])=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[N:9]([CH2:19][CH2:20][F:21])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[F:23][C:3]1[C:2]([N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)=[CH:22][C:6]2=[N:7][C:8]3[N:9]([CH2:19][CH2:20][F:21])[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

4

Reactant 2

HCID 531671-MethylpiperazineHCID 20063275HCID 20063275, compound

Product 1

HCID 20063292HCID 20063292, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 1.2 g of 8-chloro-7-fluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid in 12 cm3 of pyridine and 3.52 g of 1-methylpiperazine is heated, with stirring, at a temperature close to 110° C. for 6 hours. The reaction mixture is concentrated under reduced pressure (20 kPa) at about 60° C. The residue is taken up in 15 cm3 of water and 2 cm3 of acetic acid. A small amount of insoluble matter is removed by filtration through diatomaceous silica. 6 cm3 of 20% aqueous potassium hydroxide solution are added to the filtrate. A very small amount of insoluble matter is again removed by filtering through diatomaceous silica. 0.6 cm3 of acetic acid is added to the filtrate. The precipitate obtained is drained, washed with twice 5 cm3 of water and twice 5 cm3 of ethanol and recrystallized twice from 10 cm3 of dimethylformamide each time. 0.6 g of 7-fluoro-1-(2-fluoroethyl)-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid melting at 306°-308° C.

Workup

  1. temperatureis heated
  2. customclose to 110° C. for 6 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at about 60° C
  4. customA small amount of insoluble matter is removed by filtration through diatomaceous silica
  5. addition6 cm3 of 20% aqueous potassium hydroxide solution are added to the filtrate
  6. customA very small amount of insoluble matter is again removed
  7. filtrationby filtering through diatomaceous silica
  8. addition0.6 cm3 of acetic acid is added to the filtrate
  9. customThe precipitate obtained
  10. washwashed with twice 5 cm3 of water and twice 5 cm3 of ethanol
  11. customrecrystallized twice from 10 cm3 of dimethylformamide each time

Sources & evidence

ORD record
ord-d21e508400a44658bbb7b8a0dd6c4b25
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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