Cl[CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH:8]([CH3:12])[CH2:7][CH:6]1[CH3:13])=[O:4].[S-:14][C:15]#[N:16].[K+].[I-].[Na+].C(O)C>C1C=CC=CC=1>[S:14]([CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH:8]([CH3:12])[CH2:7][CH:6]1[CH3:13])=[O:4])[C:15]#[N:16]1-(α-Chloroacetyl)-2,4,6-trimethylpiperidine (18 grams; 0.9 mol), potassium thiocyanate (18 grams; 0.2 mol), sodium iodide (a few crystals) and ethanol (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated at reflux for a period of about 3 hours. After this time the mixture was cooled and filtered. The filtrate was evaporated leaving a solid product. The solid was then extracted with two 150 ml portions of hot benzene. The extracts were combined and evaporated under reduced pressure to yield an oil. This oil was refined by chromatography using Fuller's earth as an adsorbent and benzene as the elluent. The first 1000 ml of eluent were collected from the column and were stripped of benzene to yield 1-(α-thiocyanoacetyl)-2,4,6-trimethylpiperidine as a yellow oil having a refractive index of 1.5183 at 25° C. and having the following elemental analysis as calculated for C11H18N2OS.
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