The antidepressant amitriptyline inhibits the reuptake of norepinephrine and

Chapter 22, Problem 22.53

(choose chapter or problem)

The antidepressant amitriptyline inhibits the reuptake of norepinephrine and serotoninfrom the synaptic cleft. Because the reuptake of these neurotransmitters is inhibited,their effects are potentiated; they remain available to interact with serotonin andnorepinephrine receptor sites longer and continue to cause excitation of serotonin- andnorepinephrine-mediated neural pathways. Following is a synthesis for amitriptyline. (a) Propose a mechanism for the conversion of (A) to (B).(b) Propose reagents for the conversion of (B) to (C).(c) Propose a mechanism for the conversion of (C) to (D). (Note: It is not acceptable topropose a primary carbocation as an intermediate.)(d) Propose a reagent for the conversion of (D) to amitriptyline.(e) Is amitriptyline chiral? If so, how many of the possible stereoisomers are formed inthis synthesis?