Formaldehyde → (2-Azabicyclo[2.2.1]hept-5-en-2-yl)acetonitrile

Participants

Reaction Steps

A solution of aminoacetonitrile hydrochloride (18.5 g, 0.20 mol) in water at 5° C. is treated with 37% formalin (23.0 g, 0.28 mol formaldehyde) followed by cyclopentadiene (26.0 g, 0.4 mol), stirred at 5°-10° C. for 30 minutes and diluted with methylene chloride. The phases are separated, the aqueous phase is extracted with methylene chloride and basified to pH >12 with 10% NaOH. The aqueous basic phase is extracted with methylene chloride. The methylene chloride extract of the basic aqueous phase is concentrated in vacuo to give the title product (N-cyanomethylazanorbornene), 22.7 g, which can be distilled at 68°-70° C./0.55 torr. The compound is identified by NMR and mass spectral analyses.

Provenance & Evidence