Here are some relevant threads
Post 465442
(Rhodium: "Hydroamination Route to Amphetamines", Chemistry Discourse)Post 204565 (missing)
(obituary: "Bu-Li catalyst", Chemistry Discourse)Post 186651 (missing)
(Dope_Amine: "Attempted Hydroamination of Safrole", Novel Discourse)Post 42374 (missing)
(CHEM_GUY: "The damn text.", Novel Discourse)Below I reposted what I feel are the main two reactions of interest from this article.
Tetrahedron, Vol. 52, yr 2000, pages 5157-62
General procedure
The amine (2.5 mmol) was dissolved in 5 ml dry tetrahydrofuran in an Ace-pressure tube under an argon atmosphere. 20 mol% n-butyllithium (1.6 M n-BuLi solution in hexane) was added slowly at room temperature. The solution was stirred for 10 min and then allylbenzene (5 mmol) was added. The intensive coloured solutions were reacted for 20h at the defined temperature. After cooling to room temperature, the solution was quenched with 2 ml water, whereby a discolouration of the solution was observed. The products were isolated by acidification of the mixture with 5 ml of 1 M HCl followed by addition of 5 ml dichloromethane. The resulting aqueous phase was collected and the organic phase was extracted three times with 5 ml of 1 M HCl. The combined aqueous phases were neutralized with solid Na2CO3 and were extracted five times with 5 ml dichloromethane. The organic phases were washed with water and dried over MgSO4. After removal of the solvent in vacuo the products were isolated by column chromatography.
N-benzylamphetamine (5).
According to the general procedure benzylamine (2.5 mmol; 273 ul) and allylbenzene (5 mmol; 662 ul) were reacted in the presence of 20 mol% n-BuLi solution (0.5 mmol; 313 ul) at 50°C. The residue was purified by column chromatography (n-hexane/ethyl acetate=4:1) to afford 5 as a colourless oil. Yield: 65%(GC); 60%(isolated)
N-Butylamphetamine (7).
According to the general procedure n-butylamine (2.5 mmol; 247 ul) and allylbenzene (5 mmol; 662 ul) were reacted in the presence of 20 mol% n-BuLi solution (0.5 mmol; 313 ul) at 50°C. The residue was purified by column chromatography (n-hexane/ethyl acetate=1:2) to afford 7 as a colourless oil. Yield: 62%(GC); 54%(isolated)
Misc from article:
Tertiary (double alkylated) amines were produced in yields <1% in the reactions of allylbenzene with primary amines. This makes the method especially attractive for the selective synthesis of `secondary amphetamines' because typical nucleophilic substitution procedures with primary amines gave mixtures of secondary, tertiary and even quaternary amines. Furthermore, the reaction of benzylamine is noteworthy, since the benzyl group is easily removed by hydrogenation with H2/Pd/C to give 1-phenyl-2-aminopropane in 65% overall yield by GC analysis.
They give some conflicting data about the effect of temperature on the reaction. With piperazine the highest yeild occurs when the rxn is started at -78C and allowed to rise to room temperature. When aminating with morpholine the yeild is 44% at room temperature and 88% at 50C. They conclude that higher temperatures are better for yeild, in general, which in my opinion is totally unjustified based on the results they present. I have a suspicion that colder temperatures will increase the yeild(in THF) and would definately recommend that anyone attempting this try it cold also.(maybee even -78C)
They even state "Oligomers of beta-methylstyrene are obtained as side-products by an anionic polymerization reaction. The amount of oligomers increases at higher reaction temperature."
What would bee the best scheme for purifying the product from this reaction if it were performed on say Asarone to yeild N-benzylTMA-2. You'll have a bunch of unreacted Asarone, your N-benzylTMA-2, some polymer and possibly a bit of tertiary amine. Do you think an A/B followed by catalytic removal of the benzyl group and then a standard workup would bee sufficient?
Foxy just rambleing
This article might bee useful also
Synthesis of beta-Phenylethylamines from Styrene Derivatives
Tetrahedron Letters, Vol.39, 28 (1998) p.5073