Water → HCID 19814318, compound

HRID 466612Notes

Reaction equation

HRID 466612 reaction equation
[CH3:1][NH2:2].[CH2:3]([N:10]1[CH2:21][CH2:20][C:13]2([O:17][C:16](=O)[O:15][C:14]2=[CH2:19])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[CH2:3]([N:10]1[CH2:21][CH2:20][C:13]2([O:17][C:16](=[O:15])[N:2]([CH3:1])[C:14]2=[CH2:19])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 19814218HCID 19814218, compound

Product 1

HCID 19814318HCID 19814318, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of 1.6 g of methylamine in 35 ml of xylene prepared at 0° C. is flown to the solution of 13.0 g of 8-benzyl-4-methylene-2-oxo-1,3-dioxa-8-azaspiro[4,5]decane in 30 ml of xylene under stirring. The reaction is exothermic, thus the temperature of the reaction mixture increases up to 55° to 60° C. Thereafter, the heterogeneous reaction mixture is heated to a temperature of 100° to 102° C., maintained at the same temperature for 10 minutes, then 0.2 g of p-toluenesulfonic acid monohydrate is added to the solution and the reaction mixture is boiled while the water formed in the reaction is azeotropically distilled out. After termination of the reaction the mixture is cooled down to room temperature, washed with 5% by weight aqueous sodium hydroxide solution and after separation the xylene phase is washed to neutral with water. The organic phase is dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue is recrystallized from a mixture of ethanol and diisopropyl ether under clarifying by activated carbon to obtain the title compound in 96.7% yield, m.p.: 96°-97° C.

Workup

  1. temperaturethus the temperature of the reaction mixture increases up to 55° to 60° C
  2. temperatureThereafter, the heterogeneous reaction mixture is heated to a temperature of 100° to 102° C.
  3. temperaturemaintained at the same temperature for 10 minutes
  4. customformed in the reaction
  5. distillationis azeotropically distilled out
  6. customAfter termination of the reaction the mixture
  7. washwashed with 5% by weight aqueous sodium hydroxide solution
  8. customafter separation the xylene phase
  9. washis washed to neutral with water
  10. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue is recrystallized from a mixture of ethanol and diisopropyl ether under clarifying by activated carbon

Sources & evidence

ORD record
ord-26bb43a778ec47d387b60ba84a8c2471
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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