Phenylethanolamine → HCID 23322157, compound

HRID 280300Notes

Reaction equation

HRID 280300 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH2:17]>C1C=CC=CC=1>[CH: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)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1000PhenylethanolamineHCID 131580881-[4-(Propan-2-yl)phenyl]propan-2-one

Product 1

HCID 23322157HCID 23322157, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-isopropylphenylacetone (2.64 g) and 2-hydroxy-2-phenylethanamine (2.05 g) were refluxed in benzene (70 ml) under Dean & Stark conditions for 4 h. The solvent was removed under reduced pressure, replaced with ethanol (100 ml) and the solution hydrogenated using Pt as catalyst. The filtered solution was evaporated and the residual oil chromatographed on Kieselgel 60 (150 g). Elution with 2% methanol-chloroform gave the title compound as an oil (3.92 g). Treatment of this with a methanolic solution of fumaric acid and recrystallisation of the solid from ethylacetate gave the title compound (58:42 mixture of diastereoisomers) as the hemi fumarate containing one mole of water, mp 55-57.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe filtered solution was evaporated
  3. customthe residual oil chromatographed on Kieselgel 60 (150 g)
  4. washElution with 2% methanol-chloroform

Sources & evidence

ORD record
ord-713133e0127e4dd299f82ac7d0648219
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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