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

HRID 434364Notes

Reaction equation

HRID 434364 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 241BenzeneSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-541523cccbff4fa2a34e96a373f22372
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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