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 is slowly add thionylchloride (17 mL, 233 mmole). The dark reaction mixture is warmed to 70° C. for 20 min. The reaction is cooled and then suspended in water followed by filtration. The filtrate is extracted once with diethylether. The aqueous layer is separated and the basified with 30% NaOH solution. The product is then extracted twice with CH2Cl2, washed once with brine, dried (Na2SO4), filtered and the solvent removed to produce a crude brown liquid which is distilled (2-4 mmHg, 62°-64° C.) to give the title compound (8.0 g).

1. customThe dark reaction mixture
2. temperatureThe reaction is cooled
3. filtrationfollowed by filtration
4. extractionThe filtrate is extracted once with diethylether
5. customThe aqueous layer is separated
6. extractionThe product is then extracted twice with CH2Cl2
7. washwashed once with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customthe solvent removed
11. customto produce a crude brown liquid which
12. distillationis distilled (2-4 mmHg, 62°-64° C.)

ORD record

ord-999ea1b9c2684d8195398f791d66f315

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05104876