N,N-Dimethyl-1,3-propanediamine → HCID 15052357, compound

Participants

Reaction Steps

Acetone semicarbazone (23 g) and 3-dimethylaminopropylamine (24.5 g) were heated to 175° C. over 40 minutes, then cooled and partitioned between t-butyl methyl ether and brine. The ether layer was concentrated to give 13.2 g waxy solid 2-isopropylidene-N-(3-dimethylaminopropyl)hydrazinecarboxamide (mp 49°-53° C.). Of this, 2.0 g was boiled 8 hr. in water maintained at a volume of 20 ml, then treated with 1.67 ml 12N HCl and concentrated in vacuo to give 2.5 g crude N-(3-dimethylaminopropyl)hydrazinecarboxamide dihydrochloride as a syrup. One fifth of the latter was reacted with 5-nitro-2-furaldehyde (0.282 g) in 6 ml 1:1 methanol-ethanol containing 0.16 ml pyridine at reflux for 30 minutes. The mixture was cooled and treated with 10 ml isopropanol to give 0.51 g of the title compound as a yellow solid, mp 200°-202° C. (dec.).

Provenance & Evidence