Ethanol → N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine

HRID 2164121노트

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HRID 2164121 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12](=[O:15])[CH2:13]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([NH:30][C:31]1[CH:47]=[CH:46][C:34]([O:35][CH2:36][CH2:37][NH:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:33][CH:32]=1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(O)(C)C>[CH2:39]([N:38]([CH2:37][CH2:36][O:35][C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:27](=[O:29])[CH3:28])=[CH:47][CH:46]=1)[CH2:13][C:12](=[O:15])[C:11]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 126818023,4-Dibenzyloxyphenacyl bromideHCID 22750197N-[2-(4-acetamidophenoxy)ethyl]benzylamine

생성물 1

HCID 22750181N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine수율 66.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 3,4-dibenzyloxyphenacyl bromide (32.8 g.), N-[2-(4-acetamidophenoxy)ethyl]benzylamine (22.8 g.), anhydrous sodium carbonate (8.4 g.) and ethanol (1 liter) was boiled under reflux for 2 hours, then filtered hot to remove the inorganic sediment and evaporated in vacuo to afford a thick syrup. The latter was dissolved in hot isopropanol and the solution cooled, the precipitated solid then being collected by filtration. To a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate, and the solution was then allowed to cool to room temperature. The crystallized solid was collected by filtration, washed in diethyl ether and dried. Recrystallization from an isopropanol/ethyl acetate mixture afforded N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine (32.8 g.), m.p. 104°-6° C.

후처리

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered hot
  3. customto remove the inorganic sediment
  4. customevaporated in vacuo
  5. customto afford a thick syrup
  6. temperaturethe solution cooled
  7. filtrationthe precipitated solid then being collected by filtration
  8. additionTo a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate
  9. filtrationThe crystallized solid was collected by filtration
  10. washwashed in diethyl ether
  11. customdried
  12. customRecrystallization from an isopropanol/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-c3665fc7f8b540e087153ea11768c273
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04137328

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