Oxalic Acid → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-fluorophenyl)piperazine oxalate

HRID 64873

反応式

HRID 64873 の反応式
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>CN(C)C=O>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)=[N:6][O:7][C:8]=2[CH:13]=1

参加物

7

反応物 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

生成物 1

HCID 135207331-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(4-fluorophenyl)piperazine oxalate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5.0 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 4.0 g of 1-(4-fluorophenyl)piperazine, 10 g of potassium carbonate and a few crystals potassium iodide in 70 ml of dimethylformamide was stirred at 80° C. for 4.5 hr. The mixture was cooled, filtered and concentrated to an oil, which was stirred with water and extracted with ethyl acetate-ether. The organic extracts were washed with water (2×), saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated. The residue was purified by column chromatography (silica gel, tetrahydrofuran) to give an oil. The oil was converted to 4.5 g (45%) of product by treatment with oxalic acid. Two recrystallizations from ethyl acetate/methanol gave the analytical sample, mo 186°-187° C. (dec).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil, which
  4. extractionextracted with ethyl acetate-ether
  5. washThe organic extracts were washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, tetrahydrofuran)
  10. customto give an oil
  11. customTwo recrystallizations from ethyl acetate/methanol
  12. customgave the analytical sample, mo 186°-187° C. (dec)

出典と根拠

ORDレコード
ord-ab3f0d82e4be403ea50296641c73b690
出典データセット
uspto-grants-1986_09
特許番号
US04610988

関連ノート

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