Methyl iodide → HCID 21435861, compound

HRID 2397520Notes

Reaction equation

HRID 2397520 reaction equation
[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][NH:8][C:7](=[O:10])[CH2:6][CH2:5][CH2:4]1)[CH3:2].[H-].[Na+].[CH3:21]I>C1C=CC=CC=1>[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][N:8]([CH3:21])[C:7](=[O:10])[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12665501HCID 12665501, compound

Product 1

HCID 21435861HCID 21435861, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
40 °C

Procedure

6-Ethyl-6-(m-methoxyphenyl)hexahydro-2H-azepin-2-one (19.6 g) in dry benzene (200 ml.) was added dropwise to a stirred refluxing suspension of sodium hydride (60% suspension in oil; 4.0 g.) in dry benzene (200 ml.) under nitrogen. After the addition had been completed the reaction mixture was heated under reflux for 4 hours and then cooled to 40° C. Methyl iodide (20 ml.) was then added and the mixture stirred and heated at 40°-55° C. overnight. After cooling, the reaction mixture was washed with water, dried over magnesium sulphate and evaporated to an orange oil which was crystallised. The product was recrystallised from light petroleum (b.p. 80°-100° C.) to give 6-ethyl-6-(m-methoxyphenyl)-1-methylhexahydro-2H-azepin-2-one (19.1 g) as colourless crystals, m.p. 69°-71° C. (Found: C, 73.2; H, 8.9; N, 5.4%. C16H23NO2 requires: C, 73.5; H, 8.9; N, 5.4 %)

Workup

  1. temperaturerefluxing
  2. additionAfter the addition
  3. temperaturewas heated
  4. temperatureunder reflux for 4 hours
  5. temperatureheated at 40°-55° C. overnight
  6. temperatureAfter cooling
  7. washthe reaction mixture was washed with water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated to an orange oil which
  10. customwas crystallised
  11. customThe product was recrystallised from light petroleum (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-fc312169cd7a406c81d240749895c179
Source dataset
uspto-grants-1977_05
Patent number
US04022764

Reaction notes

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