Methods for the synthesis of polycyclic guanidine compounds
The present invention provides methods for the synthesis of polycyclic guanidine compounds. In certain embodiments, provided methods include the step of contacting a described reagent with a triamine compound to provide a polycyclic guanidine compound.
1. A method of synthesizing 1,5,7-triazabicyclo[5.5.0]dece-5-ene (TBD) comprising the step of contacting an acyclic guanidine compound with bis(3-aminopropyl)amine.
2. The method of claim 1 , wherein the step of contacting comprises heating a neat mixture of the reactants.
3. The method of claim 2 , wherein the mixture is heated to a temperature between about 80° C. and about 180° C.
4. The method of claim 1 , wherein a molar ratio between acyclic guanidine compound and bis(3-aminopropyl)amine is about 1:1.
5. The method of claim 1 , wherein the acyclic guanidine compound comprises an adduct or salt of guanidine.
6. The method of claim 1 , wherein the acyclic guanidine compound is guanidine hydrochloride.
7. The method of claim 1 , wherein the acyclic guanidine compound is a guanidine salt selected from the group consisting of: guanidine carbonate; guanidine sulfate; guanidine acetate; guanidine nitrate; guanidine p-toluene sulfonate; guanidine hydrochloride; and guanidine phosphate.
8. The method of claim 7 , wherein the step of contacting bis(3-aminopropyl)amine with a guanidine salt comprises heating a neat mixture of the reactants to a temperature between about 80° C. and about 180° C.
9. The method of claim 6 , wherein a molar ratio between guanidine hydrochloride and bis(3-aminopropyl)amine is about 1:1.
10. The method of claim 6 , wherein guanidine hydrochloride and bis(3-aminopropyl)amine are contacted in the absence of a solvent.