4-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol → N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

HRID 434361Notes

Reaction equation

HRID 434361 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][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=1)[CH2:15][NH2:16]>C(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][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 129448344-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenolHCID 204938341-[4-(Hydroxymethyl)phenyl]propan-2-one

Product 1

HCID 20493832N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (1.64 g) and 2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl) ethanamine (1.23 g) in ethanol (80 ml) was refluxed 0.5 hours, cooled to ambient temperature, platinum oxide (0.1 g) added and the mixture hydrogenated at 75 psi and 50°-60° for 8 hours. The solution was filtered, evaporated, the residue taken up in ethyl acetate and filtered again. Removal of the solvent gave the title compound as an oil which was finally obtained as a hard foam, (52:48 mixture of diastereoisomers) from ethyl acetate-benzene.

Workup

  1. temperaturewas refluxed 0.5 hours
  2. filtrationThe solution was filtered
  3. customevaporated
  4. filtrationfiltered again
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-bb3c89cce54448f78d6a061351387d2d
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

Loading…