Sodium Bicarbonate → 6-Methoxy-3,3-dimethyl-2,3,4,5-tetrahydropyridine

HRID 2216609Notes

Reaction equation

HRID 2216609 reaction equation
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.[CH3:10][C:11]1([CH3:18])[CH2:16][NH:15]C(=O)[CH2:13][CH2:12]1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:10][C:11]1([CH3:18])[CH2:12][CH2:13][C:6]([O:7][CH3:9])=[N:15][CH2:16]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 104796605,5-Dimethylpiperidin-2-one

Product 1

HCID 219413936-Methoxy-3,3-dimethyl-2,3,4,5-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium tetrafluoroborate (97%, 11.9 g, 78 mmol) was added to the dry dichloromethane (156 mL) solution of 5,5-dimethyl-2-piperidone (9.93 g, 78 mmol) at room temperature and stirred for 14 h. The reaction mixture was neutralized with 10% sodium hydrogen carbonate aqueous solution, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×120 mL), then the combined organic layer was washed with 10% sodium hydrogen carbonate aqueous solution and brine. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the titled compound was obtained as pale yellow oil (9.0 g, 82.0%).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×120 mL)
  3. washthe combined organic layer was washed with 10% sodium hydrogen carbonate aqueous solution and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a73e4dd8d374f6cb4e784410f83beb0
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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