Piperidine → HCID 131730096, compound

HRID 2191074Notes

Reaction equation

HRID 2191074 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=O)[CH2:6][C:4](=[O:5])[CH2:3]1.[C:11](#[N:17])[CH:12]([CH2:14][C:15]#[N:16])[OH:13].N1CCCCC1>CCO>[CH3:10][C:2]1([CH3:1])[CH2:3][C:4](=[O:5])[CH2:6][C:7](=[C:14]([C:15]#[N:16])[CH:12]([OH:13])[C:11]#[N:17])[CH2:9]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 31358DimedoneHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 131730096HCID 131730096, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of dimedone (98.0 g, 700.0 mmol) and malonitrile (46.2 g, 700.0 mmol) in EtOH (400 mL) at r.t. was added piperidine (8.5 g, 9.9 mL, 100.0 mmol) dropwise over 15 minutes. The reaction mixture was then heated to reflux for 3 days before cooling. The solvent was removed in vacuo and the residue was re-dissolved in EtOAc (500 mL) and dried (MgSO4). Filtration and concentration in vacuo gave a black oil that was purified by column chromatography (SiO2, 1:6 MeOH/DCM) to give the title compound as a yellow solid (108.0 g, 82%). δH (DMSO-d6) 8.31 (2H, br. s), 2.51 (2H, t, J 1.8 Hz), 2.30 (2H, s), 1.04 (6H, s). LCMS (ES−) 187.3 (M−H)−.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 3 days
  3. temperaturebefore cooling
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was re-dissolved in EtOAc (500 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration in vacuo
  8. customgave a black oil that
  9. customwas purified by column chromatography (SiO2, 1:6 MeOH/DCM)

Sources & evidence

ORD record
ord-172877ed06e245e9b5541c788493485d
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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