57 - Organic Chemistry

Question

Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.

Step-by-Step Solution

Answer

Fentanyl

It is used for the treatment of patients having severe pain and it relieves the pain after the surgery.

 

Formation of products

The reaction of (2-bromoethyl)benzene with piperidin-4-one forms A as shown below:

                                           Formation of A

The reaction of A with pyridine in the presence of mild acid forms B as shown below:

                                            Formation of B

The reaction of B with   forms C as shown below:

                                           Formation of C

The reaction of C with propionyl chloride in the presence of pyridine forms fentanyl as shown below:

                                      Formation of fentanyl