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

HRID 2049322ノート

反応式

HRID 2049322 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd8ca4e3291040bc8a98a4af6770cefd
出典データセット
uspto-grants-1980_04
特許番号
US04197241

反応ノート

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