Bromine → 2-Bromo-6-(piperidine-1-carbonyl)-cyclohexanone

HRID 1753926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753926
[N:1]1([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]Br>C(OCC)C>[Br:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[C:10]1=[O:15]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 134131852-(1-Piperidinylcarbonyl)cyclohexanone

Produkt 1

HCID 666798302-Bromo-6-(piperidine-1-carbonyl)-cyclohexanoneAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(piperidine-1-carbonyl)-cyclohexanone (19) (4.0 g, 19 mmol) was dissolved in diethyl ether (5 mL) and cooled to 0° C. under N2. Bromine (5.9 g, 19 mmol, 1.0 mL) was added dropwise over 15 min and the reaction mixture was allowed to warm to room temperature over 90 min. The solid was collected by filtration to give 5.86 g (quantitative) of 2-bromo-6-(piperidine-1-carbonyl)-cyclohexanone (20) as a white solid which was used in the next step without purification. The structure, was confirmed by 13C NMR (75 MHz, DMSO-d6) δC 17.3, 24.2, 25.3, 25.8, 32.5, 44.0, 51.6, 108.3, 145.5, 167.8.

Aufarbeitung

  1. temperatureto warm to room temperature over 90 min
  2. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-11b1807dc5354f389e1116db7cbaf9cf
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168317B2

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