Potassium Iodide → HCID 19814281, compound

HRID 466605Notes

Reaction equation

HRID 466605 reaction equation
[CH2:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:5][C:4](=[O:12])[N:3]1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+].[I-].[K+]>C(C(C)=O)C>[CH2:23]([N:9]1[CH2:10][CH2:11][C:6]2([O:5][C:4](=[O:12])[N:3]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[C:2]2=[CH2:1])[CH2:7][CH2:8]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 516892Sodium BicarbonateHCID 19814257HCID 19814257, compound

Product 1

HCID 19814281HCID 19814281, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 11.8 g of 4-methylene-3-(1-naphthyl)-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane, 5.8 ml of benzyl chloride, 4.2 g of anhydrous sodium hydrogen carbonate, 0.5 g of potassium iodide and 177 ml of methyl ethyl ketone is refluxed under argon while stirring for 18 hours. After termination of the reaction the mixture is cooled down and the solvent is evaporated under reduced pressure. After adding chloroform and water to the residue and separating the phases, the organic layer is washed with water to chloride-free, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After recrystallizing the residue under clarifying by activated carbon the title substance is obtained in 84% yield, m.p.: 130°-131° C.

Workup

  1. temperatureis refluxed under argon
  2. customAfter termination of the reaction the mixture
  3. temperatureis cooled down
  4. customthe solvent is evaporated under reduced pressure
  5. additionAfter adding chloroform and water to the residue
  6. customseparating the phases
  7. washthe organic layer is washed with water to chloride-free
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customAfter recrystallizing the residue
  11. customis obtained in 84% yield, m.p.: 130°-131° C.

Sources & evidence

ORD record
ord-62e466a0d4a94393929e0ed47c18e28c
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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