Homoveratrylamine → N-[2-(3,4-Dimethoxyphenyl)ethyl]-2-hydroxy-2-phenylacetamide

HRID 368998

Reaction equation

HRID 368998 reaction equation
[C:1]([O:11]C)(=O)[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][NH2:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][NH:25][C:1](=[O:11])[CH:2]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[OH:3])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

3

Reactant 2

HCID 8421HomoveratrylamineHCID 78066(+-)-Methyl mandelate

Product 1

HCID 596397N-[2-(3,4-Dimethoxyphenyl)ethyl]-2-hydroxy-2-phenylacetamide

Procedure

33.2 g (0.2 Mol) of methyl mandelate and 72 g (0.4 Mol) of 2-(3,4-dimethoxyphenyl)-ethylamine are heated to 160-165° C. under an N2 atmosphere with stirring, for 5 hours using a descending condenser (to remove the methanol released). The cooled residue is dissolved in 300 ml of ethyl acetate, washed twice with 100 ml of 2N HCl, once with saturated NaHCO3 solution and saturated NaCl solution, dried over MgSO4 and distilled off from the solvent.

Workup

  1. customto remove the methanol
  2. dissolutionThe cooled residue is dissolved in 300 ml of ethyl acetate
  3. washwashed twice with 100 ml of 2N HCl, once with saturated NaHCO3 solution and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. distillationdistilled off from the solvent

Sources & evidence

ORD record
ord-dcac017363dc466e9fefe95c7fe9a456
Source dataset
uspto-grants-2000_10
Patent number
US06136819

Linked notes

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