Hydrochloric Acid → HCID 21506798, compound

HRID 1287855Notes

Reaction equation

HRID 1287855 reaction equation
[NH:1]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH2:9][CH2:8]2)[C:2]1=[O:18].[H-].[Na+].S(OCC)(O[CH2:25][CH3:26])(=O)=O.Cl>CN(C)C=O>[CH2:25]([N:1]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH2:9][CH2:8]2)[C:2]1=[O:18])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6163Diethyl SulfateHCID 179282,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trioneHCID 24758Sodium hydride

Product 1

HCID 21506798HCID 21506798, compoundYield 128.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 24.3 grams (0.1 M) of 2,3-dihydrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione in 300 milliliters of dry dimethylformamide maintained under nitrogen atmosphere was added with stirring 4.37 grams (0.1 M) of a 55 per cent suspension of sodium hydride in mineral oil. After stirring for five minutes, 16.0 grams (0.1 M) of diethyl sulfate were added in one portion. The slightly exothermic reaction mixture was allowed to stir for a short time and concentrated hydrochloric acid was added dropwise until the reaction mixture was slightly acidic. The reaction solvent was removed under reduced pressure at steam bath temperature and the resulting oil extracted into ether. The ether extracts were washed with 5 percent sodium hydroxide solution, water, and then dried (MgSO4). After filtration, the ether was removed, leaving a residue, which was recrystallized from diethyl ether to give 34.9 grams (64%) of 1'-ethyl-2,3-dihydrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione, melting point 85.5°-89° C.

Workup

  1. additionwas added
  2. additionwas added dropwise until the reaction mixture
  3. customThe reaction solvent was removed under reduced pressure at steam bath temperature
  4. extractionthe resulting oil extracted into ether
  5. washThe ether extracts were washed with 5 percent sodium hydroxide solution, water
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration
  8. customthe ether was removed
  9. customleaving a residue, which
  10. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-9270429a0ab54c6992aa61be44f0ebcd
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

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