Pempidine is aganglion-blocking drug, first reported in 1958 by two research groups working independently, and introduced as an oral treatment forhypertension.[1]
Reports on the "classical" pharmacology of pempidine have been published.[2][3] The Spinks group, atICI, compared pempidine, itsN-ethyl analogue, andmecamylamine in considerable detail, with additional data related to several structurally simpler compounds.[2]
Hall's method involved reactingacetone with ammonia in the presence ofcalcium chloride to give 2,2,6,6-tetramethyl-4-piperidone, which was then reduced under Wolff–Kishner conditions, followed byN-methylation of the resulting 2,2,6,6-tetramethylpiperidine withmethylp-toluenesulfonate.
^Leonard NJ, Hauck Jr FP (October 1957). "Unsaturated amines. X. The mercuric acetate route to substituted piperidines, Δ2-tetrahydropyridines and Δ2-tetrahydroanabasines".Journal of the American Chemical Society.79 (19):5279–5292.doi:10.1021/ja01576a056.
^The boiling point of 147 °C given by these authors for their 1,2,2,6,6-pentamethylpiperidine is significantly below the range of approximately 182–188 °C reported by other chemists.
