Piperidine → 1-(piperidin-1-yl)butane-1,3-dione

HRID 1184023Notes

Reaction equation

HRID 1184023 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]=[C:8]1[O:11][C:10](=[O:12])[CH2:9]1>O1CCCC1>[N:1]1([C:10](=[O:12])[CH2:9][C:8](=[O:11])[CH3:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12661Diketene

Product 1

HCID 2467741-(piperidin-1-yl)butane-1,3-dioneYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of piperidine (4.94 ml, 50 mmol) in dry tetrahydrofuran (100 ml) at room temperature was added 4-methyleneoxetan-2-one (3.8 ml, 50 mmol) dropwise. The reaction mixture was stirred for 24 hours at room temperature, then the solvent removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase was poured into a separatory funnel and washed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine. The organic phase was separated and the solvent removed under reduced pressure to provide 1-(piperidin-1-yl)butane-1,3-dione (8.5 g, 100%) as a viscous oil. 1H NMR (CDCl3, 400 MHz) δ 3.56 (2H, app t); 3.54 (s, 2H); 3.24 (2H, app t); 2.28 (s, 3H); 1.70-1.5 (m, 6H). The compound was utilized in the next reaction without purification.

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. additionThe organic phase was poured into a separatory funnel
  4. washwashed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  5. customThe organic phase was separated
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c8876d1eb9094e1fa156ff3bebf9a0b1
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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