N-Formylpiperidine is an organic compound with the formula C₆H₁₁NO. It is the amide of formic acid

Formic acid

Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...

 and piperidine

Piperidine

Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom...

. It can be used as a polar aprotic solvent, with better hydrocarbon solubility than other amide solvents such as dimethylformamide

Dimethylformamide

Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...

 (DMF). It has also been used to transfer the formyl group to a Grignard reagent:

PhCH₂CH₂MgCl + C₆H₁₁NO → PhCH₂CH₂CHO

In some formylation reaction

Formylation reaction

A formylation reaction in organic chemistry is the catch-all name for any organic reaction in which an organic compound is functionalized with a formyl group .Aromatic formylation reactions via electrophilic aromatic substitution include:...

of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.