So basically I'm at a loss as to how to proceed. I started with the idea of converting the primary alcohol into an aldehyde and that is where I stoped. I understand that each substituent of the Nitrogen is somehow made from B, C and D and that the cynaonitrile is supposed to help you make the amide and the Gringnard Reagent is for adding a methyl group somewhere, maybe to C. Im completely at a loss and I'm just getting frustrated now :(


You seem to have got the uses of the compounds right, but could not bring that knowledge together to apply it here. As you said, you first use the Grignard to add a methyl group to D

production of K

Let's call this compound K. Then, we use $\ce{NaCN}$ to convert the alcohol into a nitrile, then to a carboxylic acid rather than an amide, as this would be easier to work with for us.

production of L

Let's call this compound L. Now we are ready to start creating the actual compound. Nitrate C and then reduce it to create the amine and reduce the ketone.

2nd to last step

Then add L to the product, followed by K. This order is followed as adding the alcohol before the acid may create a tertiary amine rather than the amide we need.

Final Step

  • $\begingroup$ I think you could expand on how to add K to the final intermediate, just adding the amide to the alcohol is not going to work. $\endgroup$ – Waylander Nov 22 '20 at 7:59
  • $\begingroup$ Oh this is great I understand now! I think I was trying to be too complicated by trying to make an amide first and then adding substituents to it. For the final part is it all just substitution reactions? $\endgroup$ – Chem Geek Nov 22 '20 at 13:08
  • $\begingroup$ @ChemGeek addition of L should be a simple acid-base neutralization, but as pointed out by Waylander addition of K might not be as simple as I think it is. I'll update the answer once I'm 100% sure $\endgroup$ – Aniruddha Deb Nov 22 '20 at 13:15
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    $\begingroup$ @AniruddhaDeb I think I would reverse the steps by forming the amide last and forming the secondary amine by a reductive amination on p-MeO-acetophenone $\endgroup$ – Waylander Nov 22 '20 at 13:35
  • $\begingroup$ Unfortunately, Chem Geek might believe that cyanide may displace hydroxide, and that water will hydrolyze a nitrile to a carboxylic acid. Does tin effect a Clemmensen reduction? How is the amide prepared? Melting the aniline and L together? The last alkylation is not detailed enough. $\endgroup$ – user55119 Nov 22 '20 at 15:56

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