1-Methylpiperazine → Ofloxacin

HRID 851080

반응식

HRID 851080 반응식
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[F:1][C:2]1[C:3]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23

참가 물질

4

반응물 2

HCID 531671-MethylpiperazineHCID 5342788,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid

생성물 1

HCID 4583Ofloxacin수율 42.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

1.0 g of 9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid and 2.85 g of N-methylpiperazine were added to 15 ml of dimethylsulfoxide. The mixture was stirred at a temperature of from about 100° to 110° C. (bath temperature) for 12 hours and the reaction mixture was concentrated to dryness in vacuo and 40 ml of water was added to the residue. Then the product was extracted with chloroform. The extract was dried and concentrated to dryness in vacuo. The residue was recrystallized from ethanol to provide 550 mg of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid as colorless needles with m.p. 250°-257° C. (with decomposition).

후처리

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo and 40 ml of water
  2. additionwas added to the residue
  3. extractionThen the product was extracted with chloroform
  4. customThe extract was dried
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-30f75383d3c446b3a5495f9e39deb37a
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382892

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