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

HRID 901100

Reaktionsgleichung

Reaktionsgleichung von HRID 901100
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 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a suspension of (bromomethyl)cyclopropane (500 mg, 4 mmol, 1.0 eq.) and 4-piperidone hydrate hydrochloride (579 mg, 4 mmol, 1.0 eq.) in acetonitrile (30 mL) was added sodium carbonate (1.148 g, 11 mmol, 3. eq.). 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 (62%) of the tide 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-a2ae8eef1ddf4083bab3acff954328f8
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361682B2

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