Glyoxal → Ammonia

Participants

Reaction Steps

The present invention also relates to a process for the preparation of 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosane (1) which comprises: reacting in a non-reactive gas atmosphere a mixture of tris(2-aminoethyl)amine (tren), isopropyl alcohol (i-PrOH) and triethylamine (Et3N) with glyoxal with a first cooling of the mixture to between about −70° C. and −30° C., wherein the glyoxal is added slowly to the mixture, to prepare 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosa, 4,6,13,15,21,23-hexaene (2); allowing the mixture including compound (2) to warm to room temperature; cooling the mixture including compound (2) with a second cooling; reacting compound (2) in a second mixture with an alkali metal in the presence of ammonia to form compound (1) from compound (2); allowing the second mixture to warm to room temperature with removal of the ammonia; and separating compound (1) from the reaction mixture.

Provenance & Evidence