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

HRID 500446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500446
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.C(=O)(O)[O-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([N:6]1[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Produkt 1

HCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazineAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (cis)-2,6-dimethylpiperazine (900 mg, 8.49 mmol) and sodium bicarbonate (0.2 ml of saturated solution) in THF (5 ml) was added benzyl bromide (1.02 ml, 8.49 mmol). The mixture was exposed to microwave irradiation at 80° C. for 15 minutes. The solvent was removed in vacuo and the residue was washed with sodium bicarbonate solution and extracted with dichloromethane. The residue was purified by flash chromatography eluting with 5-10% (v/v) methanol in dichloro-methane to afford 1-N-benzyl-(cis)-3,5-dimethylpiperazine as a clear oil (900 mg, 4.40 mmol).

Aufarbeitung

  1. customirradiation at 80° C. for 15 minutes
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. customThe residue was purified by flash chromatography
  6. washeluting with 5-10% (v/v) methanol in dichloro-methane

Quellen und Nachweise

ORD-Eintrag
ord-0831377fd2064077964211892e15656a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772227B2

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