Methanol → 4-Hydroxy-N-(2-phenylethyl)benzenepropanamide

HRID 1165121Notes

Reaction equation

HRID 1165121 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([O:17][C:18]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=O)C(=O)C1.CO.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>O>[OH:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][C:18]([NH:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:17])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1001Phenethylamine2×HCID 24243Trisodium PhosphateHCID 99557N-Succinimidyl-3-(4-hydroxyphenyl)propionate2×

Product 1

HCID 5688824-Hydroxy-N-(2-phenylethyl)benzenepropanamideYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

β-Phenylethylamine is derivatized with Bolton-Hunter reagent as follows. β-Phenylethylamine and Bolton-Hunter reagent were mixed in equimolar quantities in a 1:1 solution of methanol and sodium phosphate buffer (1M, pH 8). After 30 minutes, an excess of water was added. A crystalline solid was collected, washed with water and dried in vacuo giving 1-[3-(4-hydroxyphenyl)-propionylamino]-2-(phenyl) ethane in 75% yield.

Workup

  1. customA crystalline solid was collected
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-abbc806d550649e5968c8b049bf8ce29
Source dataset
uspto-grants-1990_03
Patent number
US04908322

Reaction notes

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