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

HRID 394095

Reaktionsgleichung

[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

Reaktionsbedingungen

Temperatur: 78 °C

Versuchsvorschrift

To a solution of 137 mL (1.3 moles) of tert-butylamine in 700 mL of toluene was added solution of 70 g (0.260 moles) of 1-ethyl-1-methyl-4-oxopiperidinium iodide and 2.18 g (0.026 moles) of NaHCO3 in 100 mL of water. The mixture was stirred at 78° C. for 6 h. After it had cooled to rt, the layers were separated and the aq layer was washed with three 200 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and concentrated to an oil that purified by distillation under reduced pressure. Fractions distilling at 72° C. at 3 mm were collected to afford the title compound as a colorless liquid. 1H NM(CDCl3, 500 MHz): δ 1.15 (s, 9H), 2.45 (t, 4H, J=6.1 Hz), 2.86 (t, 4H, J=6.1H); Mass spectrum (ESI) 156 (M+1).

Aufarbeitung

temperatureAfter it had cooled to rt
customthe layers were separated
washthe aq layer was washed with three 200 mL portions of ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated to an oil
distillationthat purified by distillation under reduced pressure
distillationFractions distilling at 72° C. at 3 mm
customwere collected

Quellen und Nachweise

ORD-Eintrag: ord-375eb11d20fd412ca3859f1fc127a98e
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06809199B2

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