1-Butanaminium, N,N,N-tributyl-, azide

UsesTetrabutylammonium azide can be used as a reagent for the synthesis of: Heteroarylannulated bicyclic morpholinesCyanimide-based inhibitors of cathepsin CTrimethylene carbonateAerobic oxidative transformation of primary azides to nitrilesSubstitution reactions at tetracoordinate boronIt is also used as a catalyst for cyclic carbonate formation.

PreparationIn a dry reaction flask, a solution of NaN3 (1.00 g, 15.4 mmol) in water (2.3 mL) was added to tetrabutylammonium hydroxide (40% aqueous solution, 2.00 g, 7.69 mmol). The resulting reaction mixture was stirred at room temperature for several hours. After the reaction was complete, dichloromethane (12 mL) was slowly added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (3 × 4 mL). All organic layers were combined and dried on anhydrous magnesium sulfate. The reaction mixture was filtered to remove the drying agent, and the resulting filtrate was concentrated under vacuum to remove the organic solvent. The residue obtained was the target product molecule, tetrabutylammonium azide.