Chemical Properties
white crystalline powder
Uses
N-(2-Hydroxyethyl)phthalimide is used as a reagent to synthesize (-)-R-rolipram is a phosphodiesterase 4 inhibitor that is used to treat depression. N-(2-Hydroxyethyl)phthalimide is also used as a reagent to synthesize FR252921, a compound that acts as an immunosuppressant. Amlodipine Impurity 6
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 4, p. 106, 1963
The Journal of Organic Chemistry, 24, p. 1122, 1959
DOI: 10.1021/jo01090a601
General Description
N-(2-Hydroxyethyl)phthalimide is the precursor for chloromethyl ethers used in the synthesis of purine acyclic nucleosides.
Synthesis
A synthetic method of N-(2-Hydroxyethyl)phthalimide. It was prepared by allowing 147.2g (1.0 mole) of phthalimide to react in an autoclave with 53.0g (1.20 moles) of ethylene oxide in the presence of 1.47g (1%) of active chromium III tri-2-ethylhexanoate (COT) and 400 ml of methylisobutyl ketone (MiBK) at 160° to 165°C for two hours. On cooling, the N-(2-Hydroxyethyl)phthalimide crystallized and was collected by filtration. A 94.7% yield of the hydroxyethyl imide was obtained.
