Ethanol → N-[2-(4-Acetylphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

HRID 434364노트

반응식

HRID 434364 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH2:17].C(O)C>C1C=CC=CC=1.[Pt]=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:17][CH2:16][CH:15]([OH:14])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 702EthanolHCID 1000PhenylethanolamineHCID 122541111-(4-Acetylphenyl) propan-2-one

생성물 1

HCID 18627896N-[2-(4-Acetylphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 241Benzene용매

실험 절차

A mixture of 1-(4-acetylphenyl) propan-2-one (10.9 g) and 2-hydroxy-2-phenylethanamine (8.5 g) in benzene (200 ml) was refluxed for 4 hours under Dean and Stark conditions. The solvent was replaced with ethanol (200 ml), platinum oxide (200 mg) was added and the mixture was hydrogenated at ambient temperature and pressure for 6 hours. The solution was filtered and the filtrate was evaporated and chromatographed on silica gel 60 (400 g) eluting with 1% methanol/chloroform. The first fraction (9.0 g) was crystallised from ether to give the title compound as a 9:91 mixture of diasteroisomers m.p. 120°-135°.

후처리

  1. temperaturewas refluxed for 4 hours under Dean and Stark conditions
  2. additionwas added
  3. customwas hydrogenated at ambient temperature
  4. filtrationThe solution was filtered
  5. customthe filtrate was evaporated
  6. customchromatographed on silica gel 60 (400 g)
  7. washeluting with 1% methanol/chloroform
  8. customThe first fraction (9.0 g) was crystallised from ether

출처 및 근거

ORD 기록
ord-541523cccbff4fa2a34e96a373f22372
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04396627

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