Шаблон:Chembox4-Chlorobutyronitrile is the organic compound with the formula ClCH2CH2CH2CN. With both chloro and cyano functional groups, it is a bifunctional molecule. It is a colorless liquid.
Cyclopropyl cyanide is prepared by reaction of 4-chlorobutyronitrile with sodium amide in liquid ammonia.[2] However an increased yield was reported when the base/solvent mixture was changed to NaOH/DMSO.[3]
4-Chlorobutyronitrile has been used as a starting material to prepare 2-Phenylpyrrolidine [1006-64-0]. This in turn is a chief precursor to a family of compounds called pyrroloisoquinolines. These are valuable agents in medicinal chemistry that are endowed with BAT subtrate reuptake inhibitor properties, elevating the synaptic concentration of serotonin and/or catecholamines. They therefore have application in the treatment of CNS diseases and eating disorders. A list of all of the known codenamed examples includes the following: JNJ-7925476, McN5652, Mcn-5292, Mcn 5707, McN-5908, McN 4612-z, McN-5558 & McN-5847.
More recently, an alternative synthetic protocol was also reported by Maryanoff.[7]
↑Craig, L. C., Bulbrook, Helen., Hixon, R. M. (May 1931). "A GENERAL METHOD OF SYNTHESIS FOR ALPHA-SUBSTITUTED PYRROLINES AND PYRROLIDINES". Journal of the American Chemical Society. 53 (5): 1831–1835. doi:10.1021/ja01356a028.
↑Zhang, Y., Kong, D., Wang, R., Hou, G. (2017). "Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines". Organic & Biomolecular Chemistry. 15 (14): 3006–3012. doi:10.1039/C7OB00442G.
↑"N-VINYLPYRROLIDIN-2-ONE AS A 3-AMINOPROPYL CARBANION EQUIVALENT IN THE SYNTHESIS OF SUBSTITUTED 1-PYRROLINES: 2-PHENYL-1-PYRROLINE". Organic Syntheses. 75: 215. 1998. doi:10.15227/orgsyn.075.0215.
