# Synthesis of Desoxypipradrol



## Jack (Dec 22, 2021)

The original synthesis of Desoxypipradrol as written in the patent linked below is effected by the condensation of Diphenyl acetonitrile with 2 Bromo pyridine followed by hydrolysis of the nitrile and decarboxylation and then catalytic hydrogenation of the pyridine ring with Raney Nickel. A paper was published that similarly produces nitroarylated nitriles with the use of alkali metal hydroxides in dimethyl sulfoxide as base. The advantage of this procedure is the omission of sodium metal alkoxides or sodium amide as used in the original patent however I cannot find literature pertaining to the condensation of aryl acetonitriles with 2 halopyridines using phase transfer catalysts or sodium hydroxide in DMSO. My question is whether the reaction is applicable here in the synthesis of the intermediate pyridine nitrile.

Synthesis of arylated acetonitriles; https://sci-hub.hkvisa.net/https://doi.org/10.1016/S0040-4020(01)90658-1
Original Patent for the synthesis of Desoxypipradrol; https://worldwide.espacenet.com/patent/search/family/004572022/publication/US2820038A?q=pn=US2820038A
A summary on Pipradrol and it's derivatives https://sci-hub.hkvisa.net/10.1016/B978-0-12-415816-0.00010-9


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## William Dampier (Jan 22, 2022)

DMSO+NaOH give a strong base, similar to sodium alkoxide (another synthesis can use K2CO3+DMSO and have good strong base effects). For this compound, need check, looks like a good idea.


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## Jack

pyridine alpha arylation of diphenylacetonitrile under phase transfer conditions;




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Sci-Hub | Rational design and synthesis of novel 2,5-disubstituted cis- and trans-piperidine derivatives exhibiting differential activity for the dopamine transporter | 10.1016/s0960-894x(01)00443-7






sci-hub.hkvisa.net


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## Jack

Here is a research paper on the synthesis of alpha 2 pyridine nitriles that uses potassium hydroxide in DMSO in yields of 60-72%




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Sci-Hub | Synthesis and molecular structure of novel 4-aryloctahydropyrido-[1,2-<em>c</em>]pyrimidine derivatives | 10.1002/jhet.5570390424






sci-hub.hkvisa.net










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