Triethylamine → HCID 19003289, compound

Participants

Reaction Steps

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of the acid chloride of Example 2 and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.1 g (0.013 mol) 2,2,6,6-tetramethyl-4-piperidinol and 2.8 g (0.028 mol) triethylamine. The reaction was then refluxed for 3 hours. The mixture was cooled and transferred to a separatory funnel with 100 ml methylene chloride, 25 ml water and 50 ml 5% sodium hydroxide. The mixture was shaken, allowed to separate and the organic phase drawn off. The aqueous phase (and interfacial solid) was extracted with an additional 25 ml solvent. The combined organic solutions were dried with anhydrous magnesium sulfate and the solvent stripped using aspirator vacuum. The product was 4.1 g of slightly yellow crystals (melting at 196°-200° C.). The infrared spectrum (chloroform) showed the carbonyl absorption at 1705 cm-1 (imide and ester). The NMR Spectrum showed the anticipated aromatic ring (7.7-7.9 ppm, doublet, 1H; 8.3-8.5, multiplet, 2H) and two HALS groups [5.2-5.7 ppm, multiplet, 1H; 4.4-4.9 ppm, multiplet, 1H; 1.0-2.3 ppm, several multiplets including two singlets (1.2 and 1.3 ppm)]. The UV spectrum showed an absorbance maximum (THF) at 296 nm, molar absorptivity 300.

Provenance & Evidence