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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: hopelesscemist on October 20, 2016, 01:50:26 PM

Title: All kinds of reactions
Post by: hopelesscemist on October 20, 2016, 01:50:26 PM
Hello,
so I am not very great at chemistry, but I have a homework from organic chemistry, that I don't know how to complete. I would be very happy for your help. Thanks in advance
So the task goes:
1-Benzylpiperidone reacts with chloro(4-chlorophenyl)magnesium, product of this (A) reaction is debezyled (B). B then reacts with 4-Bromo-N,N-dimethyl-2,2-diphenylbutanamide (+Na2CO3)
C1CC(=O)CCN1Cc1ccccc1 + c1cc(Cl)ccc1[Mg]Cl :rarrow: A
A :rarrow: B (debenzylation)
B + BrCCC(c1ccccc1)(c1ccccc1)C(=O)N(C)C :rarrow: C

So now what I've got: I think that A will be 1-Benzyl-4-phenyl-4-piperidinol (I don't think, I can make this one using SMILES, sorry), since grignard reagent should react this way with ketones..
Then B, I have no idea. I failed to find more information or debenzylation (or I found things like this: https://www.researchgate.net/figure/223613177_fig1_Fig-1-Debenzylation-reaction-structural-variability-of-substrate-and-protecting-group (https://www.researchgate.net/figure/223613177_fig1_Fig-1-Debenzylation-reaction-structural-variability-of-substrate-and-protecting-group) it describes functional groups, but none of them is same as in my case.)
Then (from the task) I know that C is medicine of some sort, but without B, I can't really continue.

I will be thankful for any help
Title: Re: All kinds of reactions
Post by: AWK on October 20, 2016, 02:32:14 PM
Debenzylation H2 on Pd/C
4-(4-chlorophenyl)-4-hydroxypiperidine or 4-(4-chlorophenyl)-4-piperidinol
Loperamide