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

HRID 1753926Notes

Reaction equation

HRID 1753926 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-11b1807dc5354f389e1116db7cbaf9cf
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

Loading…