1-Phenethylamine → N-Methylbenzylamine

Reaction equation

[CH:1]([S:14]([CH2:16][C:17]([OH:19])=[O:18])=[O:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC([CH:26]([S+]([O-])CC(N)=O)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=CC=1.C[CH:40]([NH2:47])C1C=CC=CC=1>>[CH:1]([S:14]([CH2:16][C:17]([O-:19])=[O:18])=[O:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:40][NH:47][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 3

HCID 74081-Phenethylamine

HCID 3085267Modafinil acid

HCID 178514057HCID 178514057, compound

Product 2

HCID 7669N-Methylbenzylamine

HCID 19020205(-)-Benzhydrylsulfinylacetate

Procedure

Lafon also disclosed the use of an intermediate, a racemic mixture of benzhydrylsulphinylacetic acid to prepare an isomer of modafinil in U.S. Pat. No. 4,927,855, referring to French patent 2,326,181B. The racemic mixture of the acid was reacted with the (−)-α-methylbenzylamine to provide the (−)-benzhydrylsulphinylacetate of (−)-methylbenzylamine which is acidified with concentrated hydrochloric acid to provide (−)benzyhydrylsulphinylacetic acid. The levo-acid thus produced was then reacted with methylsulfate in water and sodium bicarbonate to provide methyl(−)benzhydrylsulphinylacetate. The acetate was then amidated with ammonia gas to provide (−)benzhydrylsulphinylacetamide.