Potassium Carbonate → 1-(Methylsulphonyl)piperidin-4-one

HRID 271762

Reaktionsgleichung

Reaktionsgleichung von HRID 271762
C(=O)([O-])[O-].[K+].[K+].Cl.O.[NH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)(Cl)Cl.O>[CH3:16][S:17]([N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)(=[O:19])=[O:18]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 2723901Piperonylamine

Produkt 1

HCID 120720291-(Methylsulphonyl)piperidin-4-oneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium carbonate (324 g, 2340 mmol) was added to a solution of 4-piperidone monohydrate hydrochloride (90 g, 586 mmol) in chloroform (300 mL) and water (300 mL). The slurry was cooled to 0° C. and treated with methylsulfonyl chloride (136 mL, 1760 mmol) by dropwise addition over a 1 h period (gas evolution was observed). The reaction mixture was allowed to shake for 72 h and was partitioned between CH2Cl2 (500 mL) and saturated aqueous NaHCO3 (500 mL). The aqueous layer was extracted with CH2Cl2 (3 ×200 mL). The organic layer was washed with 1% KHSO4 (250 mL), dried (Na2SO4), and concentrated to afford 90.5 g (87%) of a white solid. MS (electrospray): exact mass calculated for C6H11NO3S, 177.1; m/z found, 178.1 [M+H]+. HPLC (reverse phase conditions): tR=2.19 min. 1H NMR (400 MHz, CDCl3): 3.60 (t, J=6.5 Hz, 4H), 2.89 (s, 3H), 2.59 (t, J=6.3 Hz, 4H).

Aufarbeitung

  1. customwas partitioned between CH2Cl2 (500 mL) and saturated aqueous NaHCO3 (500 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3 ×200 mL)
  3. washThe organic layer was washed with 1% KHSO4 (250 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-264273c7bb81420794cb570aead93579
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452890B2

Verknüpfte Notizen

Wird geladen…