Sodium Carbonate → 1-(Cyclopropylmethyl)piperidin-4-one

HRID 272557

Reaktionsgleichung

Reaktionsgleichung von HRID 272557
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.Cl.O.[NH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH:5]1([CH2:4][N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 2723901Piperonylamine

Produkt 1

HCID 180021811-(Cyclopropylmethyl)piperidin-4-oneAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a suspension of bromomethyl cyclopropane (4 mmol) and 4-piperidone hydrate hydrochloride (4 mmol) in acetonitrile (30 mL) was added sodium carbonate (11 mmol). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100%).

Aufarbeitung

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with acetonitrile
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

Quellen und Nachweise

ORD-Eintrag
ord-6f8c09e36221499a9402e63f834e28db
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456174B2

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