Piperidine → 2-(1-Piperidinylcarbonyl)cyclohexanone

HRID 628706Notes

Reaction equation

HRID 628706 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10]CC)=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[N:13]1([C:8]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]2=[O:1])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 134131852-(1-Piperidinylcarbonyl)cyclohexanoneYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-oxocyclohexane-carboxylate (5.3 g, 31 mmol, 5.0 mL) DMAP (1.05 g, 9.4 mmol) and piperidine (5.3 g, 63 mmol, 6.2 mL) in toluene (100 mL) were heated at reflux for 4 days. The reaction was allowed to cool and the reaction was concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (20-80% (B), 100 g, 8 CV, 85 mL/min) to afford 6.26 g (96%) of 2-(piperidine-1-carbonyl)-cyclohexanone (19) as a white solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 23.5, 24.5, 25.5, 26.2, 27.1, 30.4, 41.9, 42.9, 46.8, 54.2, 167.6, 207.6.

Workup

  1. temperatureat reflux for 4 days
  2. temperatureto cool
  3. concentrationthe reaction was concentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with petrol (A) and ethyl acetate (B) (20-80% (B), 100 g, 8 CV, 85 mL/min)

Sources & evidence

ORD record
ord-04ffb312f42e407d9e6e9f26cb0dcfea
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

Loading…