N-Formylpiperidine Explained

N-Formylpiperidine is an organic compound with the formula C₆H₁₁NO. It is the amide of formic acid and piperidine. It can be used as a polar aprotic solvent, with better hydrocarbon solubility than other amide solvents such as dimethylformamide (DMF).^[1] It has also been used to transfer the formyl group to a Grignard reagent:

PhCH₂CH₂MgCl + C₆H₁₁NO → PhCH₂CH₂CHO

In some formylation reaction of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.^[2]

Notes and References

1. Book: Kirk‑Othmer Encyclopedia of Chemical Technology . Pyridine and Pyridine Derivatives . Eric F. V. Scriven . Ramiah Murugan . 2005 . amp . Wiley . 10.1002/0471238961.1625180919031809.a01.pub2. 0471238961 .
2. Lidija Bondarenko . Ina Dix . Heino Hinrichs . Henning Hopf . Cyclophanes. Part LII:1 Ethynyl[2.2]paracyclophanes – New Building Blocks for Molecular Scaffolding . . 2004. 16 . 2751–2759 . 2004 . 10.1055/s-2004-834872.