i thought some of you opiophiles out there might find this interesting.
des chloro loperamide has an ED 50 of 3 mg/kg about 1/2 that of morphine; does'nt sound like much but esterify it and potency increases dramitically.
this paper gives examples of the ammonium formate palladium system for the hydrodechlorination of chloro arenes.
the preferrable way to hydrodechlorinate loperamide would be ammonium formate pd/c (as little as 3% loading is acceptable) and methanol.
stir 2 hours at room temp, filter, evaporate, basify,then extract.
the yeilds are 100% with no detectable starting material.
the process is highly chemoselective tolerating benzylic alcohols and esters so overreduction is not a concern (basically impossible to fuck up).
the paper below illustrates a hydrodechlorination using palladium on polystrene polyethylene glycol copolymer support.
and this link discusses the feasiblilty of des-chloroloperamide..
http://forum.opiophile.org/archive/index.php/t-34565.html?s=1170095548a680afaca8870c1283fddd
p.s. one thing i need clarification on is:
in one example they employ 3 equivalents of ammonium formate to reduce pentachloro arenes and in the table below they employ the same amount for mono chloro benzene what gives?
des chloro loperamide has an ED 50 of 3 mg/kg about 1/2 that of morphine; does'nt sound like much but esterify it and potency increases dramitically.
this paper gives examples of the ammonium formate palladium system for the hydrodechlorination of chloro arenes.
the preferrable way to hydrodechlorinate loperamide would be ammonium formate pd/c (as little as 3% loading is acceptable) and methanol.
stir 2 hours at room temp, filter, evaporate, basify,then extract.
the yeilds are 100% with no detectable starting material.
the process is highly chemoselective tolerating benzylic alcohols and esters so overreduction is not a concern (basically impossible to fuck up).
the paper below illustrates a hydrodechlorination using palladium on polystrene polyethylene glycol copolymer support.
and this link discusses the feasiblilty of des-chloroloperamide..
http://forum.opiophile.org/archive/index.php/t-34565.html?s=1170095548a680afaca8870c1283fddd
p.s. one thing i need clarification on is:
in one example they employ 3 equivalents of ammonium formate to reduce pentachloro arenes and in the table below they employ the same amount for mono chloro benzene what gives?