Dimethyl Sulfate → 39985-26-7

HRID 1619419Notes

Reaction equation

HRID 1619419 reaction equation
[CH3:1][CH:2]1[CH2:8][CH2:7][NH:6][C:5](=[O:9])[CH2:4][CH2:3]1.S(OC)(O[CH3:14])(=O)=O.[OH-].[K+]>CCOCC>[CH3:14][O:9][C:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:8][CH2:7][N:6]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 137496Hexahydro-5-methyl-2H-azepin-2-one

Product 1

HCID 1060683639985-26-7

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-methylazepan-2-one (1.6 g) and dimethyl sulfate (2 g, 15.9 mmol) was stirred at 120° C. for 4 h. After it was cooled to room temperature, the reaction mixture was diluted with 10 mL ether and adjusted to pH 6 with aqueous KOH. The mixture was extracted with ether (2×50 mL). The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude (E)-7-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-azepine (1.2 g) was used for the next step without further purification.

Workup

  1. temperatureAfter it was cooled to room temperature
  2. extractionThe mixture was extracted with ether (2×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude (E)-7-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-azepine (1.2 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-029b309ad3bd41ef956191c8de2b65ab
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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