Hydrazine hydrate (1:1) → 4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2475

반응식

HRID 2475 반응식
[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

참가 물질

6

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 19689983N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2f45ef41d64f43759ade38b0eb4ac1d1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728835

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