2-(3-Fluorophenyl)piperazine → (RS)-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 344854Notes

Reaction equation

HRID 344854 reaction equation
[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]2[CH2:34][NH:33][CH2:32][CH2:31][NH:30]2)[CH:26]=[CH:27][CH:28]=1>>[F:1][C:2]1[C:20]([N:33]2[CH2:32][CH2:31][NH:30][CH:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)[CH2:34]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

3

Reactant 2

HCID 34578962-(3-Fluorophenyl)piperazineHCID 111970267,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 54448567(RS)-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 86.2%

Procedure

The reaction is performed under the conditions of Example 16, but starting with 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid (1.3 g) and (RS)-2-(3-fluorophenyl)piperazine (1.8 g). After 1 recrystallization in dimethylformamide (50 cc) containing ethanol (50%), (RS)-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo -1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.74 g) is obtained in the form of a yellow solid, m.p. 254° C.

Workup

  1. customAfter 1 recrystallization in dimethylformamide (50 cc)
  2. additioncontaining ethanol (50%)

Sources & evidence

ORD record
ord-bcfbc1fc0abc4946859fee9b240a5d38
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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