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

HRID 1091379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091379
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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 665948754-((2S)-1,4-dibenzylpiperazin-2-yl)benzonitrileAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7120c25caed940808c8b6940844c9789
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129377B2

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