1-Phenethylamine → N-Methylbenzylamine

HRID 1393698Notes

Reaction equation

HRID 1393698 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

5

Reactant 3

HCID 74081-PhenethylamineHCID 3085267Modafinil acidHCID 178514057HCID 178514057, compound

Product 2

HCID 7669N-MethylbenzylamineHCID 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.

Workup

  1. additionThe racemic mixture of the acid

Sources & evidence

ORD record
ord-a9dcb013fa06465bb940febafd274a28
Source dataset
uspto-grants-2008_03
Patent number
US07345188B2

Reaction notes

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