Benzylamine → 5-Benzylamino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2291285Notes

Reaction equation

HRID 2291285 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[C:12]=3[F:14])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH2:28]([NH:35][C:9]1[C:10]([F:22])=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5][N:4]2[CH:1]1[CH2:2][CH2:3]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 13825520HCID 13825520, compound

Product 1

HCID 146641725-Benzylamino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 59.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-cyclopropyl-5,6,8-trifluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.0 g), benzylamine (420 mg), and pyridine (5 ml) was heated at 100°-110° C. for 3 hours. The reaction mixture was evaporated to dryness under reduced pressure. After addition of water to the residue, the mixture was acidified with 10% aqueous acetic acid and extracted with chloroform. The extract was dried and evaporated. The resulting crystals were recrystallized from ethanol-ether to give 5-benzylamino-1-cyclopropyl-6,8-difluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (730 mg), m.p. 132°-133° C.

Workup

  1. temperaturewas heated at 100°-110° C. for 3 hours
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. additionAfter addition of water to the residue
  4. extractionextracted with chloroform
  5. customThe extract was dried
  6. customevaporated
  7. customThe resulting crystals were recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-6bb6bef107774786a2f127e748e30d7b
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Reaction notes

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