HCID 15639027, compound → 2,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trione

HRID 1287853Notes

Reaction equation

HRID 1287853 reaction equation
[C:1]1([C:7]2([CH2:15][CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>S(=O)(=O)(O)O>[NH:9]1[C:10](=[O:13])[CH2:11][CH2:12][C:7]2([C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:17](=[O:19])[CH2:16][CH2:15]2)[C:8]1=[O:14]

Participants

3

Reactant 1

HCID 15639027HCID 15639027, compound

Product 1

HCID 179282,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trioneYield 82.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Two hundred (200) grams (0.76 M) of 3-phenyl-2,6-dioxopiperidine-3-propionic acid, prepared by the method of Koelsch, J. Org. Chem., 25, 164 (1960), and 500 ml of concentrated sulfuric acid were heated on a steam bath with stirring for 1.5 hours. The mixture was cooled to room temperature and poured over crushed ice with stirring. The light tan colored precipitate which separated was water washed and filtered. This material was combined with a second crop which separated on standing and both were stirred in water and treated with five percent sodium carbonate solution until just alkaline. The precipitate was collected and water washed. The precipitate was recrystallized from acetone to give a total of 144.6 grams (82.4%) of 2,3-dihydrospiro-[naphthalene-1(4H), 3'-piperidine]-2',4,6'-trione, melting point 198°-200° C.

Workup

  1. additionpoured
  2. customover crushed ice
  3. stirringwith stirring
  4. customThe light tan colored precipitate which separated
  5. washwashed
  6. filtrationfiltered
  7. customseparated on standing
  8. stirringboth were stirred in water
  9. additiontreated with five percent sodium carbonate solution until just alkaline
  10. customThe precipitate was collected
  11. washwater washed
  12. customThe precipitate was recrystallized from acetone

Sources & evidence

ORD record
ord-4e5bf506ad5c454f955fd115f899f858
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

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