Methyl iodide → HCID 20362684, compound

HRID 1679361Notes

Reaction equation

HRID 1679361 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][C:10](=[O:13])[NH:11][CH2:12][C:6]=2[CH:5]=1.[CH3:16]I>CN(C)C=O>[CH3:16][N:11]1[C:10](=[O:13])[CH2:9][CH2:8][C:7]2[CH:14]=[CH:15][C:4]([CH3:3])=[CH:5][C:6]=2[CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20362654HCID 20362654, compound

Product 1

HCID 20362684HCID 20362684, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.023 moles of sodium hydride is added slowly, while stirring, to a solution of 2.0 g. (0.011 moles) of 8-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one in 60 ml. of dimethylformamide, followed by heating at 80° C. for 80 minutes. The reaction mixture is cooled in an ice bath and 6.5 g. (0.046 moles) of methyl iodide added dropwise, the rate of addition being regulated so as to maintain the temperature of the reaction mixture at about 10° C. When the addition is complete, the temperature is raised slowly to 60° C. and then maintained at this level for 3 hours. The reaction mixture is evaporated to dryness in vacuo and the solid residue is extracted with chloroform. The organic solution is washed twice with water, dried over anhydrous sodium sulfate, filtered and then evaporated to dried over anhydrous sodium sulfate, filtered and then evaporated to dryness in vacuo. The solid residue is taken up in diisopropyl ether, filtered over active carbon and recrystallized from diisopropyl ether. 2,8-Dimethyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one is obtained in a yield of 55% of theory. M.P. 75°-76° C.

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. additionthe rate of addition
  3. temperatureto maintain the temperature of the reaction mixture at about 10° C
  4. additionWhen the addition
  5. temperaturethe temperature is raised slowly to 60° C.
  6. temperaturemaintained at this level for 3 hours
  7. customThe reaction mixture is evaporated to dryness in vacuo
  8. extractionthe solid residue is extracted with chloroform
  9. washThe organic solution is washed twice with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. dry with materialto dried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. customevaporated to dryness in vacuo
  16. filtrationfiltered over active carbon
  17. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8d9aefd777aa43f2bd19b8f03b980f7c
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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