水合肼 → 4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2475

反应方程式

HRID 2475 反应方程式
[F:1][C:2]1[CH:47]=[CH:46][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[O:44][CH3:45])[S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4C(=O)C5=CC=CC=C5C4=O)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.O.NN.C(=O)(O)[O-].[Na+]>CO.C1COCC1.C(OCC)(=O)C>[NH2:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([S:17]([N:16]([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:47][CH:46]=3)[CH2:9][CH2:10]2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:44][CH3:45])(=[O:19])=[O:18])=[CH:25][CH:24]=1

参与物

6

反应物 3

HCID 24654水合肼HCID 516892碳酸氢钠HCID 19689983N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide

产物 1

HCID 196898074-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide收率 76.4%

试剂、催化剂与溶剂 2

HCID 8857乙酸乙酯溶剂HCID 21899815MeOH tetrahydrofuran溶剂

实验过程

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide (77 mg, 0.117 mmol) was dissolved in a methanol-THF (3:2) mixture solution (2.5 ml) to which was subsequently added hydrazine hydrate (1 ml) while cooling in an ice bath. After 15 minutes of stirring at the same temperature, the organic solvent was removed by evaporation, and the resulting residue was extracted with methylene chloride. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium carbonate, followed by the removal of the solvent by evaporation. To the resulting residue was added an acetic acid-THF-water (3:1:1) mixture solution (3 ml). After 2 hours of stirring at room temperature, the solvent was removed by evaporation, and the resulting reaction solution was diluted with ethyl acetate (15 ml), mixed with saturated sodium bicarbonate aqueous solution (5 ml) and then extracted with ethyl acetate. After drying the extract on anhydrous sodium carbonate, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1) to obtain 47 mg (76.4%) of the title compound in a colorless oily form.

后处理

  1. temperaturewhile cooling in an ice bath
  2. customthe organic solvent was removed by evaporation
  3. extractionthe resulting residue was extracted with methylene chloride
  4. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  5. dry with materialdried on anhydrous sodium carbonate
  6. customfollowed by the removal of the solvent by evaporation
  7. additionTo the resulting residue was added an acetic acid-THF-water (3:1:1) mixture solution (3 ml)
  8. stirringAfter 2 hours of stirring at room temperature
  9. customthe solvent was removed by evaporation
  10. customthe resulting reaction solution
  11. extractionextracted with ethyl acetate
  12. customAfter drying the
  13. extractionextract on anhydrous sodium carbonate
  14. customthe solvent was removed by evaporation
  15. customthe resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

来源与证据

ORD记录
ord-2f45ef41d64f43759ade38b0eb4ac1d1
来源数据集
uspto-grants-1998_03
专利号
US05728835

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