Ammonia → 3-Ethylhexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

HRID 2049322Notes

Reaction equation

HRID 2049322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]2=[O:17])[CH:6]=[CH:7][CH:8]=1.[NH2-].[Na+].N.[CH2:21](I)[CH3:22]>C1(C)C=CC=CC=1.O.O1CCCC1>[CH2:21]([C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17])[CH3:22]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6340IodoethaneHCID 24533Sodium amideHCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

Product 1

HCID 27290973-Ethylhexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-oneYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one (4.66 g) in dry toluene (25 ml) was added dropwise to a stirred suspension of sodium amide (1.0 g) in dry toluene (50 ml). The reaction mixture was heated to reflux, ammonia was evolved and the reaction mixture became red. After refluxing for 2 hours dry tetrahydrofuran (20 ml) was added, the mixture cooled and ethyl iodide (3.7 g) added. A white precipitate was formed and the red colour rapidly disappeared. The reaction mixture was heated under reflux for 2 hours, cooled and decomposed by the addition of water. The aqueous phase was separated and the organic layer washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated affording an oil which crystallised from diisopropyl ether to give the title compound (3.29 g), m.p. 62°-64° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. additionwas added
  4. temperaturethe mixture cooled
  5. customA white precipitate was formed
  6. temperatureThe reaction mixture was heated
  7. temperatureunder reflux for 2 hours
  8. temperaturecooled
  9. customThe aqueous phase was separated
  10. washthe organic layer washed with saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulphate
  12. customevaporated
  13. customaffording an oil which
  14. customcrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-bd8ca4e3291040bc8a98a4af6770cefd
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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