Sodium Hydroxide → 2,2,N-Trimethyl-N-(4-oxocyclohexyl)propionamide

HRID 1748614Notes

Reaction equation

HRID 1748614 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]([CH3:18])[C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[Na+]>Cl>[CH3:14][C:13]([CH3:16])([CH3:15])[C:12]([N:11]([CH3:18])[CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 79111757N-(1,4-Dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide

Product 1

HCID 791196402,2,N-Trimethyl-N-(4-oxocyclohexyl)propionamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To N-(1,4-dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide (12.5 g) was added 6 N hydrochloric acid aqueous solution (50 ml), and stirred at room temperature for 1 hour. After completion of the reaction, 12 N aqueous solution of sodium hydroxide (25 ml) was added thereto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and then the solvent was evaporated. To the obtained residue was added diisopropyl ether, the insoluble matter was collected by filtration, and then dried to give the titled compound (7.25 g) as a white solid. MS (ESI) m/z: 212 (M+H)+.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. additionTo the obtained residue was added diisopropyl ether
  6. filtrationthe insoluble matter was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-46e9cf22ab3d4654993d995afa42fd7b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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