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

HRID 1506687Notes

Reaction equation

HRID 1506687 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-d0f65930f984439894b48f7e72589681
Source dataset
uspto-grants-2015_12
Patent number
US09220795B2

Reaction notes

Loading…