|Chemical and physical data|
|Molar mass||155.28 g/mol|
|3D model (Jmol)||Interactive image|
Reports on the "classical" pharmacology of pempidine have been published. The Spinks group, at ICI, compared pempidine, its N-ethyl analogue, and mecamylamine in considerable detail, with additional data related to several structurally simpler compounds.
Two early syntheses of this compound are those of Leonard and Hauck, and Hall. These are very similar in principle: Leonard and Hauck reacted phorone with ammonia, to produce 2,2,6,6-tetramethyl-4-piperidone, which was then reduced by means of the Wolff–Kishner reduction to 2,2,6,6-tetramethylpiperidine; this secondary amine was then N-methylated using methyl iodide and potassium carbonate.
Hall's method involved reacting acetone with ammonia in the presence of calcium chloride to give 2,2,6,6-tetramethyl-4-piperidone, which was then reduced under Wolff-Kishner conditions, followed by N-methylation of the resulting 2,2,6,6-tetramethylpiperidine with methyl p-toluenesulfonate.
- A. Spinks and E. H. P. Young (1958) Nat. 181 1397
- G. E. Lee et al. (1958) Nat. 181 1717.
- A. Spinks et al. (1958) Br. J. Pharmacol. Chemother. 13 501-520.
- D. F. Muggleton and H. W.Reading (1959) Br. J. Pharmacol. Chemother. 14 202
- H. K. Hall (1957) J. Am. Chem. Soc. 79 5447-5451.
- N. J. Leonard and F. P. Hauck (1957) J. Am. Chem. Soc. 79 5279-5292.
- The "trivial" name of this compound is triacetonamine.
- The boiling point of 147° given by these authors for their N,2,2,6,6-pentamethylpiperidine (pempidine) is significantly below the range of ~182–188° reported by other chemists.