N,N-Dimethyl-1,3-propanediamine → HCID 22799977, compound

Participants

Reaction Steps

cis-6-Chloro-4-phenyl-1,3-benzodioxan-2-carboxylic acid (2.91 g., 10 mmoles), ethionyl chloride (10 ml) and dry DMF (4 drops) were refluxed in 100 ml of dry CH2Cl2 for 2 hrs. Removal of solvent and excess reagent under reduced pressure afforded the crude acid chloride which was then redissolved in CH2Cl2 (50 ml) and treated with dimethylaminopropyl amine (1.53 g., 15 mmloes). The reaction was somewhat exothermic and the stirred mixture was maintained at 20° for 35 mins., and then at reflux for 45 mins. After solvent removal, the residue was partitioned between 5% Na2CO3 solution and CH2Cl2 (2 portions). The organics were then washed with brine, dried (MgSO4) and treated with HClg. Solvent removal and crystallization of the residue from isopropyl alcohol gave the product as a white solid (3.34 g., 81.3%). Recrystallization from abs EtOH:Et2O afforded pure material (mp 213° -216° d).

Provenance & Evidence