Tetrahydrofuran → N-methyl-1-(propan-2-yl)piperidin-4-amine

HRID 499717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499717
Cl.CN.C1COCC1.[CH:9]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)([CH3:11])[CH3:10].[C:19]([BH3-])#[N:20].[Na+]>C(O)(=O)C.C(O)C>[CH:9]([N:12]1[CH2:17][CH2:16][CH:15]([NH:20][CH3:19])[CH2:14][CH2:13]1)([CH3:11])[CH3:10]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 793131-(Isopropyl)-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Produkt 1

HCID 3159676N-methyl-1-(propan-2-yl)piperidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred mixture of methylamine hydrochloride (2.62 g, 38.8 mmol), THF (30 ml), ethanol (15 ml), N-isopropyl-4-piperidinone (3.0 ml, 20.2 mmol), and acetic acid (3.60 ml) was added sodium cyanoborohydride (30 ml, 1 molar solution in THF, 30 mmol), and the mixture was stirred at 60° C. for 6 hours and then at room temperature overnight. The mixture was concentrated under reduced pressure, water (50 ml) and potassium carbonate (47.0 g) were added, and the mixture was extracted with ethyl acetate (6×50 ml). The combined extracts were dried over magnesium sulphate and concentrated, to yield 3.78 g (quant.) of the title compound as an oil, which was used without further purification.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. concentrationThe mixture was concentrated under reduced pressure, water (50 ml) and potassium carbonate (47.0 g)
  4. additionwere added
  5. extractionthe mixture was extracted with ethyl acetate (6×50 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af0c3523c8bb45da8c600fd68dc14a8f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767695B2

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