Dimethylformamide → 3-Allyl-1,3-dimethyl-piperidin-4-one

HRID 576523

Reaction equation

HRID 576523 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH:4]([CH3:9])[CH2:3]1.[H-].[Na+].[CH2:12](Br)[CH:13]=C.[CH3:16]N(C=O)C>>[CH2:9]([C:4]1([CH3:16])[C:5](=[O:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]1)[CH:12]=[CH2:13]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 1073111,3-Dimethyl-4-piperidone

Product 1

HCID 137400223-Allyl-1,3-dimethyl-piperidin-4-one

Procedure

1,3-Dimethyl-piperidin-4-one (6 g, 47.24 mmol) was dissolved in 20 mL DMF and sodium hydride (2.07 g, 51.95 mmol) was added portionwise at 0° C. under nitrogen atmosphere. This was followed by dropwise addition of allyl bromide (5.71 g, 47.19 mmol) in 4 mL DMF at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at RT for 15 min, quenched with ice-water and extracted with EtOAc (3×100 mL). The organic layer was washed with water (3×100 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh) eluting with 7% EtOAc in hexane to obtain 3.2 g of 3-allyl-1,3-dimethyl-piperidin-4-one.

Workup

  1. customquenched with ice-water
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe organic layer was washed with water (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 100-200 mesh)
  7. washeluting with 7% EtOAc in hexane

Sources & evidence

ORD record
ord-8092f642c0d046c0b72ce314b3e63012
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Linked notes

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