cis-2,6-Dimethylmorpholine

clear colorless liquid

Cis-2,6-Dimethylmorpholine is used in the synthesis of p38α MAP kinase inhibitors used in the treatment of autoimmune diseases. Also used towards the synthesis of potent agonists and antagonists of 5-HT 4 receptors.

The cis-2,6-dimethylmorpholine isomer exhibits superior fungicidal activity against a broad range of fungi compared to its trans-isomer[1][2]. This compound serves as a precursor in the synthesis of pyrazolopyrimidine mTOR inhibitors, where it replaces morpholine to yield specific derivative structures[2][3].

[1] Dr. Walter Himmele, Dr. E.-H. P. (1980). 3-Phenylpropylamines, A New Class of Systemic Fungicides†. Angewandte Chemie International Edition, 19 3, 184–189. https://doi.org/10.1002/anie.198001841
[2] Gao-Fei Xu . (2016). Synthesis and fungicidal activity study of novel daphneolone analogs with 2,6-dimethylmorpholine. Chinese Chemical Letters, 27 4, Pages 555-558. https://doi.org/10.1016/j.cclet.2016.01.045
[3] Arie Zask*. (2009). Morpholine Derivatives Greatly Enhance the Selectivity of Mammalian Target of Rapamycin (mTOR) Inhibitors. Journal of Medicinal Chemistry, 52 24, 7942–7945. https://doi.org/10.1021/jm901415x