N-(2-Oxo-3-piperidyl)phthalimide → (+/-)2-(2-methoxy-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 217882Notes

Reaction equation

HRID 217882 reaction equation
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.[C:10]1(=[O:27])[N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][NH:17]C2=O)[C:13](=[O:22])[C:12]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:11]12.C(=O)([O-])O.[Na+]>ClCCl>[CH3:6][O:7][C:9]1[CH:15]([N:14]2[C:10](=[O:27])[C:11]3[C:12](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:13]2=[O:22])[CH2:20][CH2:19][CH2:18][N:17]=1

Participants

5

Reactant 3

HCID 135339N-(2-Oxo-3-piperidyl)phthalimideHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 67265802(+/-)2-(2-methoxy-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 13.474 g (91.1 mmol) of trimethyloxonium tetrafluoroborate in 294 mL of anhydrous dichloromethane was added 22.25 g (91.1 mmol) of (+/−)-3-phtalimidopiperidin-2-one (Heterocycles (1996), 42(2), 537-42, Enantiomer (2001), 6(5), 275-279, Synthesis (1991), (5), 417-20) and the resulting mixture was stirred at room temperature for 12 h. The mixture was hydrolyzed with a saturated aqueous solution of sodium hydrogen carbonate, extracted with dichloromethane, dried over sodium sulfate and the solvent was evaporated to afford 23.22 g (99%) of pure product as a yellow oil. The compound was used as such in the next step.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d4e2379ec17a490da6829c57f2829932
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

Loading…