Chemistry
Heterocyclic Building Blocks
Piperidines
(S)-N-phenylpiperidine-2-carboxamide
Acylation: The piperidine nitrogen can be acylated with various acyl chlorides or anhydrides to introduce new substituents on the amide nitrogen.
Friedel-Crafts Acylation: If you have an appropriate aromatic compound, you can perform a Friedel-Crafts acylation reaction to attach an acyl group to the phenyl ring. This can be done using Lewis acids like aluminum chloride (AlCl3) as a catalyst.
Grignard Reaction: You can react (S)-N-phenylpiperidine-2-carboxamide with a Grignard reagent (RMgX), where R is an alkyl or aryl group. This reaction can be used to form new carbon-carbon bonds.
Amide Coupling: (S)-N-phenylpiperidine-2-carboxamide can be coupled with other molecules using amide coupling agents like EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) to form amide bonds.
Nucleophilic Substitution: The piperidine ring can undergo nucleophilic substitution reactions, particularly if the piperidine nitrogen is activated. For example, it can react with alkyl halides to form N-alkylated products.
Reductive Amination: By reacting with an appropriate aldehyde or ketone in the presence of reducing agents like sodium cyanoborohydride (NaBH3CN), you can perform reductive amination to introduce new substituents on the piperidine nitrogen.
Hofmann Degradation: Treating the amide with sodium hypochlorite (NaOCl) and sodium hydroxide (NaOH) can result in the Hofmann degradation, leading to the formation of the corresponding primary amine.
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(S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide