Hydroxyamine hydrochloride → 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzonitrile

HRID 1091379노트

반응식

HRID 1091379 반응식
Cl.[NH2:2]O.[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@@H:12]1[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[OH-].[Na+].C(O)C>[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@@H:12]1[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:2])=[CH:26][CH:25]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 866345574-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehyde

생성물 1

HCID 665948754-((2S)-1,4-dibenzylpiperazin-2-yl)benzonitrile수율 64.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14798Sodium Hydroxide용매

실험 절차

Hydroxylamine hydrochloride (0.5 g, 7.75 mmol) was added to a solution of 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehyde (2.2 g, 5.94 mmol) in 1N aqueous sodium hydroxide (10 ml) and ethanol (10 ml) at room temperature and stirred for 2 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in acetic acid (10 ml) and was stirred at 80° C. for 6 hours. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzonitrile (1.4 g, 64%) as a colorless oil.

후처리

  1. customThe mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in acetic acid (10 ml)
  6. stirringwas stirred at 80° C. for 6 hours
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
  9. washThe organic layer was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel column chromatography
  13. washeluting 5-10% methanol in chloroform

출처 및 근거

ORD 기록
ord-7120c25caed940808c8b6940844c9789
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129377B2

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