Benzyl Chloride → (R)-1-Benzyl-3-methylpiperazine

HRID 1951738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951738
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.[OH-].[Na+]>[CH2:8]([N:6]1[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 73304342-Methylpiperazine, (R)-

Produkt 1

HCID 6923226(R)-1-Benzyl-3-methylpiperazineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (10 mmol) (R)-2-methylpiperazine, 1.3 g (10 mmol) benzyl chloride and 4.1 g (30 mmol) potassium carbonate in 10 ml ethanol was heated at reflux over night. After cooling to room temperature the reaction mixture was diluted with a 0.5 M aqueous solution of sodium hydroxide and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. Flash column chromatography gave 0.93 g (49%) of the title compound as an off-white solid. MS m/e (%): 191 (M+H+, 100)

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. extractionextracted with three portions of dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb47dae0217b480a83c0b6e5ccfe3434
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404708B2

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