Propylenediamine → HCID 178470249, compound

To a solution of propane-1,2-diamine (5.7 mL, 66.4 mmol) in ethanol (100 mL) was added dropwise diethyl ketomalonate (10 mL, 65.6 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr, and then stirred for 1 day with heating under reflux. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a small amount of ethanol, and the solution was passed through silica gel (150 g, eluent, hexane:ethyl acetate=1:1→ethyl acetate). The eluate was concentrated under reduced pressure, and the precipitate was collected by filtration, and washed with diisopropyl ether to give the title compound (2.27 g, 19%) as a pale-orange powder. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=1:1→ethyl acetate) to give the title compound (726 mg, 6.1%) as a pale-yellow powder.

1. stirringstirred for 1 day
2. temperaturewith heating
3. temperatureunder reflux
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. dissolutionthe residue was dissolved in a small amount of ethanol
6. concentrationThe eluate was concentrated under reduced pressure
7. filtrationthe precipitate was collected by filtration
8. washwashed with diisopropyl ether

ORD record

ord-69c6264138ca427db857099a076ead6e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486965B2