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Chapter 18: Problem 42

Procaine (its hydrochloride is marketed as Novocain) was one of the first local anesthetics for infiltration and regional anesthesia. See Chemical Connections: "From Cocaine to Procaine and Beyond." According to the following retrosynthetic scheme, procaine can be synthesized from 4-aminobenzoic acid, ethylene oxide, and diethylamine as sources of carbon atoms.

Short Answer

Expert verified
Answer: The main steps in the synthesis of procaine from 4-aminobenzoic acid, ethylene oxide, and diethylamine are: 1. React 4-aminobenzoic acid with ethylene oxide under basic conditions to form 4-(2-hydroxyethylamino)benzoic acid. 2. React 4-(2-hydroxyethylamino)benzoic acid with diethylamine to form an ester linkage between the carboxylic acid and diethylamine, resulting in procaine.

Step by step solution

01

Identify 4-aminobenzoic acid, ethylene oxide, and diethylamine

In this reaction, we are given the starting materials as 4-aminobenzoic acid, ethylene oxide, and diethylamine. First, it's important to identify their structures: 4-aminobenzoic acid: C6H4(NH2)COOH Ethylene oxide: C2H4O Diethylamine: (C2H5)2NH We'll use these structures to analyze possible reaction mechanisms.
02

React 4-aminobenzoic acid with ethylene oxide

We will first react 4-aminobenzoic acid (C6H4(NH2)COOH) with ethylene oxide (C2H4O). The amino (-NH2) group from 4-aminobenzoic acid will attack the electrophilic carbon of ethylene oxide through a nucleophilic attack. The product will be a new compound with a chain of two carbons from ethylene oxide attached to the nitrogen group of 4-aminobenzoic acid. This reaction takes place under basic conditions. Product 1: 4-(2-hydroxyethylamino)benzoic acid C6H4(NHCH2CH2OH)COOH
03

React product 1 with diethylamine

Now, we react product 1 (4-(2-hydroxyethylamino)benzoic acid, C6H4(NHCH2CH2OH)COOH) with diethylamine ((C2H5)2NH). This reaction results in an esterification process. The -OH group of the carboxylic acid and one of the hydrogen atoms from the nitrogen in diethylamine will be removed to create water. A new bond forms between the carboxylic acid carbon and the diethylamine nitrogen, resulting in an ester. Final product: Procaine C6H4(NHCH2CH2OH)COO(C2H5)2N
04

Summary of steps

To synthesize procaine from 4-aminobenzoic acid, ethylene oxide, and diethylamine, follow these steps: 1. React 4-aminobenzoic acid with ethylene oxide under basic conditions to form 4-(2-hydroxyethylamino)benzoic acid. 2. React 4-(2-hydroxyethylamino)benzoic acid with diethylamine to form an ester linkage between the carboxylic acid and diethylamine to produce procaine. The synthesis of procaine from these starting materials involves the nucleophilic attack by the amino group and subsequent esterification with diethylamine.

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Most popular questions from this chapter

Predict the distribution of oxygen-18 in the products obtained from hydrolysis of ethyl benzoate labeled in the ethoxy oxygen under the following conditions. (a) In aqueous NaOH (b) In aqueous \(\mathrm{HCl}\) (c) What distribution would you predict if the reaction were done with the tert-butyl ester in \(\mathrm{HCl}\) ?

Reaction of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. Propose a mechanism for this reaction.

The following statements are true experimental observations. Explain the reason behind each observation. (a) The reaction of acetic acid with ammonia in water does not give any amide products. (b) The reaction of acetyl chloride with water causes the \(\mathrm{pH}\) to decrease. (c) The hydrolysis of an amide at neutral pH takes seven years at room temperature, while the hydrolysis of an acid chloride takes a few minutes.

Propose a synthesis for diphenhydramine starting from benzene, benzoic acid, and 2- \((N, N-\) dimethylamino) ethanol.

Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid and 2-methylpiperidine and any other necessary reagents.
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