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

HRID 1629594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629594
[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, 1083, 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-360008357dbf4055a129ef71a1995469
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08790619B2

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