N

16.1.3 Alkylamines

Chlorpheniramine: Chlorpheniramine, 3-(p-chlorophenyl)-3-(2-pyridyl)propyldimethy-lamine (16.1.12), is synthesized in two ways. The first is from 4-chlorbenzylcyanide, which is reacted with 2-chlorpyridine in the presence of sodium amide to form 4-chlorphenyl (2-pyridyl)acetonitrile (16.1.10). Alkylating this with 2-dimethylaminoethylchloride in the presence of sodium amide gives 7-(4-chlorphenyl)-7-cyano-MN-dimethyl-2-pyridine-propanamine (16.1.11), the hydrolysis and decarboxylation of which lead to chlorpheniramine (16.1.12) [20].

NaNH2 CH3

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