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

HRID 628707Notes

Reaction equation

HRID 628707 reaction equation
[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]

Participants

4

Reactant 2

HCID 24408BromineHCID 134131852-(1-Piperidinylcarbonyl)cyclohexanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-8ac4b54ee90045deb91566dc0ec8c0cc
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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