Thionyl Chloride → HCID 22914803, compound

Temperature

70 °C

The starting material, 1,2,6-trimethyl-4-piperidinol, may be prepared by the method disclosed in Archi Kem, Volume 27, pages 189°-192 (1955). To a cooled (ice-bath) solution of 1,2,6-trimethyl-4-piperidinol (12.2 g, 85.3 mmol) in 120 mL of dry benzene was slowly added thionylchloride (17 mL, 233 mmole). The dark reaction mixture was then warmed to 70° C. for 20 min. The reaction was cooled and then suspended in water followed by filtration. The filtrate was extracted once with diethylether. The aqueous layer was separated and then basified with 30% NaOH solution. The product was then extracted twice with CH2Cl2, washed once with brine, dried (Na2SO4), filtered and solvent removed to give a crude brown liquid which was distilled (2-4 mmHg, 62°-64° C.) to give the title compound (8.0g, 58% yield).

1. customdisclosed in Archi Kem, Volume 27, pages 189°
2. customThe dark reaction mixture
3. temperatureThe reaction was cooled
4. filtrationfollowed by filtration
5. extractionThe filtrate was extracted once with diethylether
6. customThe aqueous layer was separated
7. extractionThe product was then extracted twice with CH2Cl2
8. washwashed once with brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customsolvent removed
12. customto give a crude brown liquid which
13. distillationwas distilled (2-4 mmHg, 62°-64° C.)

ORD record

ord-8790ef552fd44dd18d6247925620b043

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05089496