| Drug Name: | alpha-Eucaine |
| Iupac Name: | Methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate |
| Width: | 150 |
| Tradename: | Alpha-Eucaine |
| Cas Number: | 470-68-8 |
| Pubchem: | 5282357 |
| Kegg: | C14166 |
| Chebi: | 35059 |
| Chemspiderid: | 4445520 |
| Synonyms: | α-Eucaine; Eucaine A |
| C: | 19 |
| H: | 27 |
| N: | 1 |
| O: | 4 |
| Stdinchi: | 1S/C19H27NO4/c1-17(2)12-19(16(22)23-6,13-18(3,4)20(17)5)24-15(21)14-10-8-7-9-11-14/h7-11H,12-13H2,1-6H3 |
| Stdinchikey: | MJMZACWQGQGLBI-UHFFFAOYSA-N |
| Smiles: | CC1(CC(CC(N1C)(C)C)(C(=O)OC)OC(=O)C2=CC=CC=C2)C |
α-Eucaine (alpha-eucaine) is a drug that was previously used as a local anesthetic.[1] It was designed as an analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic.[2]
The Aldol condensation between two equivalents of acetone gives Mesityl oxide [141-79-7] (1) (isophorone is a side-product of this reaction). Ammonolysis of mesityl oxide formed diacetonamine [625-04-7] (2). The reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone [826-36-8] (3). N-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one [5554-54-1] (4). Cyanohydrin formation gives CID:434556 (5). Esterification of the tertiary alcohol with benzoyl chloride gives (6). Pinner reaction of the nitrile with EtOH/H+ affords alpha-eucaine (7).