Benzyl Bromide → (3r,5s)-1-Benzyl-3,5-dimethylpiperazine

HRID 493329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493329
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH2:9]([N:6]1[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Produkt 1

HCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazineAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an ice cold (˜0° C.) suspension of cis-2,6-dimethylpiperazine (4.0 g, 35 mmol) in DMF (100 mL) was benzyl bromide (6.0 g, 35.0 mmol) added in portions under a period of 45 min and the reaction mixture was stirred at room temperature for 48 h. The solvent was evaporated from the suspension and the residue was dissolved in aqueous HCl and washed twice with CHCl3. The aqueous phase was made alkaline and extracted twice with CHCl3. The combined organic phases were washed with H2O and brine, dried (MgSO4), and concentrated to give 4.9 g (68%) of the title product as a colorless oil.

Aufarbeitung

  1. additionadded in portions under a period of 45 min
  2. customThe solvent was evaporated from the suspension
  3. dissolutionthe residue was dissolved in aqueous HCl
  4. washwashed twice with CHCl3
  5. extractionextracted twice with CHCl3
  6. washThe combined organic phases were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b7c649c98b3d412a9c958c7d82409a47
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

Notizen zur Reaktion

Wird geladen…