Dimethyl Sulfate → HCID 21506801, compound

HRID 1287854Notes

Reaction equation

HRID 1287854 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].C[O-].[Na+].S(OC)(O[CH3:26])(=O)=O>CN(C)C=O>[CH3:26][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]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 179282,3-Dihydro-4H-spiro[naphthalene-1,3'-piperidine]-2',4,6'-trioneHCID 10942334Sodium Methoxide

Product 1

HCID 21506801HCID 21506801, compoundYield 17.5%

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 100 milliliters of dry dimethylformamide was added with stirring 5.4 grams (0.1 M) of sodium methoxide. This was followed by 17.0 milliliters of dimethyl sulfate. The reaction mixture became clear and was slightly exothermic. After stirring for 15 minutes, 50 milliliters of solvent was removed at reduced pressure on a steam bath. The resulting solution was cooled and added to 1 liter of ice water. The resulting precipitate was collected and washed with 5 per cent sodium hydroxide solution and finally with water. Recrystallization from butanone-petroleum ether (70°-90°) and then from aqueous ethanol gave 18.4 grams (17.5%) of 1'-methyl-2,3-dihydrospiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione, melting point 136°-137.5° C.

Workup

  1. custom50 milliliters of solvent was removed at reduced pressure on a steam bath
  2. temperatureThe resulting solution was cooled
  3. additionadded to 1 liter of ice water
  4. customThe resulting precipitate was collected
  5. washwashed with 5 per cent sodium hydroxide solution and finally with water
  6. customRecrystallization from butanone-petroleum ether (70°-90°)

Sources & evidence

ORD record
ord-a03b1d51e81f42f3900cb9c9cec7fd94
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

Loading…