PROBLEM 7.66

Question

Question: Diphenhydramine, the antihistamine in Benadryl, can be prepared by the following two-step sequence. What is the structure of diphenhydramine?

Step-by-Step Solution

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Answer

The structure of diphenhydramine is given below

diphenhydramine

1Diphenhydramine

It is an antihistamine used in Benadryl to get relief from the symptoms of allergies, hay fever, and common cold.

It is also used sometimes for the treatment of vomiting and dizziness caused by motion sickness.

2The structure of diphenhydramine

Diphenhydramine can be prepared by the following two steps:

In the first step, there is the removal of an H⁺ ion.

Removal of H⁺ ion

In the next step, the nucleophilic attack takes place, and the leaving Br^- leaves as shown in the following structures:

Formation of diphenhyramine

PROBLEM 7.65

PROBLEM 7.67

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