bwitiacumen
02-14-2005, 02:03 AM
Product From Quaternary Ammonium Compound Using Grignard?
Over the years of collecting PCP-analogue patents and journal references, I never paid any attentionOver the years of collecting PCP-analogue patents and journal references, I never paid any attention to the production of (1-Phenylcyclohexyl)dialkylamines, but while browsing through US3097136, the method of reacting a quaternary ammonium salt with a phenylmagnesium halide, then adding H2O to create active product really caught my eye!
The only example in the patent that uses this method is Example 3; The iodomethane is reacted with the cyclohexylidene-ethylamine, and now we have our quaternary ammonium “compound”(QAC). It’s referred to as being a “compound” twice in Example C, but earlier in the patent they call it a quaternary ammonium “salt”(QAS). Am I right in my assumption that QAC and QAS are the same precursor/compound??
Here’s what’s really bugging me; In the example, the (1-Phenylcyclohexyl)ethylmethylamine is obtained by reacting the quaternary ammonium compound with one mole of phenyl-lithium, and doing the usual work-up(addition of water). Why must the creators of this patent complicate my understanding of this method by using phenyl-lithium instead of the phenylmagnesium halide that was mentioned earlier in the patent? Both give the same result?
Here's link to it: http://l2.espacenet.com/espacenet/viewer?PN=US3097136&CY=ch&LG=en&DB=EPD (http://l2.espacenet.com/espacenet/viewer?PN=US3097136&CY=ch&LG=en&DB=EPD)
Over the years of collecting PCP-analogue patents and journal references, I never paid any attentionOver the years of collecting PCP-analogue patents and journal references, I never paid any attention to the production of (1-Phenylcyclohexyl)dialkylamines, but while browsing through US3097136, the method of reacting a quaternary ammonium salt with a phenylmagnesium halide, then adding H2O to create active product really caught my eye!
The only example in the patent that uses this method is Example 3; The iodomethane is reacted with the cyclohexylidene-ethylamine, and now we have our quaternary ammonium “compound”(QAC). It’s referred to as being a “compound” twice in Example C, but earlier in the patent they call it a quaternary ammonium “salt”(QAS). Am I right in my assumption that QAC and QAS are the same precursor/compound??
Here’s what’s really bugging me; In the example, the (1-Phenylcyclohexyl)ethylmethylamine is obtained by reacting the quaternary ammonium compound with one mole of phenyl-lithium, and doing the usual work-up(addition of water). Why must the creators of this patent complicate my understanding of this method by using phenyl-lithium instead of the phenylmagnesium halide that was mentioned earlier in the patent? Both give the same result?
Here's link to it: http://l2.espacenet.com/espacenet/viewer?PN=US3097136&CY=ch&LG=en&DB=EPD (http://l2.espacenet.com/espacenet/viewer?PN=US3097136&CY=ch&LG=en&DB=EPD)