Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocane
Here is a relatively straightforward synthesis of 1,5 diazocane that uses the Beckmann rearrangement as a key step. The Beckmann rearrangement is a useful synthetic tool for converting ketones to amides.  If the carbonyl is in a ring, then conversion to the amide will enlarge the ring by one nitrogen atom.



The novel twist in the following synthesis is to perform a double Beckmann rearrangement in the penultimate step.




heating benzene with concentrated sulfuric acid containing excess sulfur trioxide (oleum) will lead to the disulfonated product, benzene-1,3-disulfonic acid
heating the disulfonic acid with potassium carbonate produces resorcinol (see here)
treating resorcinol with hydrogen gas at low pressure over a rhodium catalyst yields 1,3-cyclohexanedione (see here)
hydroxylamine can be prepared by oxidizing ammonia with hydrogen peroxide to produce ammonium nitrite which can then be converted by a number of methods to hydroxylamine
the hydroxylamine is used in standard fashion to afford the bis-oxime (various oxime stereoisomers are likely produced, but this does not matter, all oxime stereoisomers will undergo the Beckmann rearrangement in the next step)
the bis-oxime is converted to the bis-amide through a double Beckmann rearrangement (see here for this specific conversion; note that the double Beckmann could afford isomers but only the desired isomer is produced; see the preceding link for the authors explanation as to why this is so)
finally, standard reduction of the bis-amide with $\ce{LiAlH4}$ and aqueous workup gives rise to the target molecule


The double Beckmann could also be run starting with 1,4-cyclohexanedione (readily prepared from benzene, see here).  1,4-cyclohexanedione has the advantage of symmetry - the first Beckmann rearrangement can produce only one isomer.  Although the second Beckmann rearrangement could produce 2 isomers, only the desired 1,5-diazocane-2,4-dione was isolated (see here).