Tert-Butylamine → 1-tert-Butyl-4-piperidone

HRID 132042

Reaktionsgleichung

Reaktionsgleichung von HRID 132042
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:1]([N:5]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodide

Produkt 1

HCID 738401-tert-Butyl-4-piperidoneAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

To a solution of t-butylamine (78.2 ml, 0.74 mol) in toluene (400 ml) was added a solution of 1-ethyl-1-methyl-4-oxopiperidinium iodide (40 g, 0.148 mol) and sodium bicarbonate (1.245 g,0.014 mol) in water (60 ml). The reaction mixture was heated at 78° C. for 6 hours and then allowed to cool to ambient temperature. The layers were separated and the aqueous layer was washed with EtOAc. The organics were combined and washed with brine,dried (MgSO4), filtered and reduced in vacuo to yield 1-tert-butyl-4-oxopiperidine (14 g) (LC/MS: Rt 0.39, [M+H]+156).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customThe layers were separated
  3. washthe aqueous layer was washed with EtOAc
  4. washwashed with brine,dried (MgSO4)
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1f0bfb08afc843dd8155cfb9fc77edc5
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385059B2

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