Zolpidem is a hypnotic drug acting on the GABA receptor complex, but which has a non-benzodiazepine pharmacophore. It may be synthesized as follows:

i) Give a mechanism for the first step

ii) Give a mechanism for the Mannich step

iii) Give a mechanism for the Hofmann Elimination and subsequent attack of cyanide 

iv) Provide a mechanism for the Cyanide FGI 

v) Is the heterocyclic ring system of Zolpidem aromatic?

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NH2 MeNH2, ACOH ELOH, A CH2O Br i) Mel ií) NaCN DIC, HOBT, HNMe2 HCI (32% v/v in H20) 180°C NC OH NH2 MeNH2, ACOH ELOH, A CH2O Br i) Mel ií) NaCN DIC, HOBT, HNMe2 HCI (32% v/v in H20) 180°C NC OH