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

HRID 2049322노트

반응식

HRID 2049322 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd8ca4e3291040bc8a98a4af6770cefd
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04197241

반응 노트

불러오는 중…