Homoveratrylamine → N-[2-(3,4-Dimethoxyphenyl)ethyl]-2-hydroxy-2-phenylacetamide
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
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
- customto remove the methanol
- dissolutionThe cooled residue is dissolved in 300 ml of ethyl acetate
- washwashed twice with 100 ml of 2N HCl, once with saturated NaHCO3 solution and saturated NaCl solution