1-Methylpiperazine → Ofloxacin

HRID 851080

反応式

HRID 851080 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 4583Ofloxacin収率 42.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30f75383d3c446b3a5495f9e39deb37a
出典データセット
uspto-grants-1983_05
特許番号
US04382892

関連ノート

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