Ethanol → N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-phenyl ethanamine

HRID 434363Notes

Reaction equation

HRID 434363 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[OH:13][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][NH2:16].C(O)C.C(O)(=O)/C=C/C(O)=O>C1C=CC=CC=1.CC(O)C.[Pt]=O>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:16][CH2:15][CH:14]([OH:13])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 1000PhenylethanolamineHCID 444972Fumaric AcidHCID 204938341-[4-(Hydroxymethyl)phenyl]propan-2-one

Product 1

HCID 20493831N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-phenyl ethanamine

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 241BenzeneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (3.0 g) and 2-hydroxy-2-phenylethanamine (2.5 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. The solution was filtered and evaporated to give an oil which was taken up in propan-2-ol and treated with the theoretical amount of fumaric acid. The title compound was obtained as the hemi-fumarate salt m.p. 67°-70° (60:40 mixture of diastereoisomers).

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. customevaporated
  6. customto give an oil which

Sources & evidence

ORD record
ord-0286394a8491401082d11930540adb02
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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