Dimethyl Sulfate → Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one

HRID 2049336Notes

Reaction equation

HRID 2049336 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:16][O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 126655233-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one

Product 1

HCID 12875111Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of hexahydro-3-(3-hydroxyphenyl)-2H-azepin-2-one (4.1 g), anhydrous potassium carbonate (5.6 g) and dimethyl sulphate (2.52 g) was heated under reflux with stirring in acetone (50 ml). After cooling the solution was filtered and evaporated to dryness under reduced pressure. The product was recrystallised from diisopropyl ether/ethyl acetate affording the title compound, identical to that obtained by the method of Example 1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter cooling the solution
  4. filtrationwas filtered
  5. customevaporated to dryness under reduced pressure
  6. customThe product was recrystallised from diisopropyl ether/ethyl acetate affording the title compound
  7. customidentical to that obtained by the method of Example 1

Sources & evidence

ORD record
ord-14d09d2b2e5748939466a7a19a4db96f
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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