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

HRID 434364ノート

反応式

HRID 434364 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 241Benzene溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-541523cccbff4fa2a34e96a373f22372
出典データセット
uspto-grants-1983_08
特許番号
US04396627

反応ノート

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