1-Methylpiperazine → HCID 14700561, compound

HRID 981211Notes

Reaction equation

HRID 981211 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][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]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

4

Reactant 2

HCID 531671-MethylpiperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 14700561HCID 14700561, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under conditions analogous to Reference Example 1 but starting from 5 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 16 g of 1-methylpiperazine in 50 cm3 of pyridine. After concentrating the reaction mixture under reduced pressure, 25 cm3 of acetic acid are added to the residue, which is suspended in 100 cm3 of water. A very small amount of insoluble matter is removed by filtration through diatomaceous silica for filtration. 200 cm3 of 3N aqueous potassium hydroxide solution are added to the filtrate and a very small amount of insoluble matter is again removed by filtration through diatomaceous silica for filtration. 5 cm3 of acetic acid are added to the filtrate. The precipitate formed is drained and washed with 3 times 50 cm3 of water. After recrystallizing twice from 17 cm3 of dimethylformamide each time, 3.2 g of 7-fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 356° C.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure, 25 cm3 of acetic acid
  2. additionare added to the residue, which
  3. customA very small amount of insoluble matter is removed by filtration through diatomaceous silica for filtration
  4. addition200 cm3 of 3N aqueous potassium hydroxide solution are added to the filtrate
  5. customa very small amount of insoluble matter is again removed by filtration through diatomaceous silica for filtration
  6. addition5 cm3 of acetic acid are added to the filtrate
  7. customThe precipitate formed
  8. washwashed with 3 times 50 cm3 of water
  9. customAfter recrystallizing twice from 17 cm3 of dimethylformamide each time, 3.2 g of 7-fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Sources & evidence

ORD record
ord-8959eef2111848e0942a8c04c0a868c7
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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