[jacknicholson]

Hi. I would be very grateful if somebody could tell me what the product is of the following reaction. Thanks.


2,4-dimethylpyridine with 1.PhOCOCl
                                     MeMgBr
                                  2. H₂/Pd/C
                                  3. NaOH/H₂O

[sjb]

I'm not 100% sure of this, so take with a pinch of salt.

Pyridine itself reacts with ClCO₂Ph to form the cationic carbamate on nitrogen, with chloride counterion. This can then react n-BuMgCl at carbon-4 to form the 1,4-dihydropyridine, which I assume you can then reduce (whether totally down to the piperidine or to the 1,2,3,4-tetrahydropyridine I'm not sure), and then -OH hydrolyses the carbamate and reforms the secondary amine.

Have a look at Org. Prep. Proc. Int., 1990, 22, 315 (Smith) and J. Org. Chem., 1982, 47, 4315 http://dx.doi.org/10.1021/jo00143a028 (Abdullah and Comins) (from Joule and Mills)

[limpet chicken]

Oooh, nasty!, I would be extremely careful handling the 1,2,3,4 tetrahydropyridine intermediate, I could see it possibly being a dopaminergic neurotoxin like N-methylphenylpyridinium+, which destroys dopaminergic neurons and causes permanent, chemically induced parkinson's disease.