4-Carbamoyl-4-phenylheptanedioic acid → 2,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trione

HRID 1287852Notes

Reaction equation

HRID 1287852 reaction equation
[C:1]([C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:5][CH2:6][C:7]([OH:9])=O)(=[O:3])[NH2:2]>S(=O)(=O)(O)O>[NH:2]1[C:12](=[O:14])[CH2:11][CH2:10][C:4]2([C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7](=[O:9])[CH2:6][CH2:5]2)[C:1]1=[O:3]

Participants

3

Reactant 1

HCID 215067884-Carbamoyl-4-phenylheptanedioic acid

Product 1

HCID 179282,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trioneYield 34.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Five (5) grams (0.0179 M) of γ-carbamoyl-γ-phenylpimelic acid prepared by the method of Koelsch, J. Org. Chem., 25, 164 (1960), in 100 ml of concentrated sulfuric acid were heated on a steam bath for two hours. The cooled reaction mixture was poured with stirring into crushed ice. The separated solid was washed with sodium bicarbonate solution. Recrystallization from 30 ml of acetone solution (treated with activated charcoal) gave 1.5 grams (34.5%) of 2,3-dihydrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured
  3. custominto crushed ice
  4. washThe separated solid was washed with sodium bicarbonate solution
  5. customRecrystallization from 30 ml of acetone solution (treated with activated charcoal)

Sources & evidence

ORD record
ord-f275db93a4cf4eb38d42f24a46494b13
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

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