三溴化硼 → 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-hydroxyphenyl)benzamide

HRID 2516

反应方程式

HRID 2516 反应方程式
[C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:26][CH2:27]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参与物

5

反应物 3

HCID 25134三溴化硼HCID 516892碳酸氢钠HCID 196899044-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

产物 1

HCID 196897984-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-hydroxyphenyl)benzamide收率 76.7%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

实验过程

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (50.0 mg, 0.10 mmol) was dissolved in methylene chloride (3.0 ml) to which was subsequently added a methylene chloride solution (1 ml) of boron tribromide (0.018 ml, 0.19 mmol) at 0° C. After 12 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1) to obtain 37.3 mg (76.7%) of the title compound in a light yellow amorphous form.

后处理

  1. extractionextracted with ethyl acetate
  2. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled off under a reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1)

来源与证据

ORD记录
ord-afe5cbc25fd340cf8536ac9ee64ce538
来源数据集
uspto-grants-1998_03
专利号
US05728835

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