Hydrochloric Acid → HCID 9840460, compound

Temperature

20 °C

To a mixture of 10 ml of toluene and 100 ml of a 50% aqueous sodium hydroxide solution were added 10 g of (-)-2-(benzo[b]thiophen-5-yl)-2-(tetrahydropyranyloxy)ethanol, 8.04 g of 2-(N,N-diethylamino)ethyl chloride hydrochloride and 610 mg of tetra-n-butylammonium hydrogensulfate, and the resulting mixture was refluxed for 1.5 hours. The reaction mixture was cooled to 20° C., and thereto were then added 90 ml of toluene and 150 ml of water, after which the organic layer formed was separated. The aqueous layer was extracted with 30 ml of toluene, and the extract obtained was combined with the organic layer previously separated, and the mixture was washed with water. Thereafter, 60 ml of water was added to the organic layer, and the pH was adjusted to 0.5 with 6N hydrochloric acid, after which the mixture was stirred at 25° C. for 1 hour. The aqueous layer was separated and washed with ethyl acetate, and thereto was added 40 ml of ethyl acetate, after which the pH was adjusted to 10.2 with potassium carbonate. The organic layer formed was separated, washed successively with water and an aqueous saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained were dissolved in 60 ml of ethyl acetate and 40 ml of acetone to form a solution. To the solution was added 7 ml of a solution of hydrogen chloride in ethanol (6.1N). The solution was stirred at 20° C. for 2 hours, and the crystals thus separated were collected by filtration to obtain 10.7 g (yield: 90%) of (-)-1-(benzo[b]thiophen-5-yl)-2-[2-(N,N-diethylamino)ethoxy]ethanol hydrochloride. This was recrystallized from ethyl acetate-ethanol to obtain colorless needle crystals having a melting point of 120°-121° C.

1. temperaturethe resulting mixture was refluxed for 1.5 hours
2. customafter which the organic layer formed
3. customwas separated
4. extractionThe aqueous layer was extracted with 30 ml of toluene
5. customthe extract obtained
6. custompreviously separated
7. washthe mixture was washed with water
8. additionThereafter, 60 ml of water was added to the organic layer
9. customThe aqueous layer was separated
10. washwashed with ethyl acetate
11. additionwas added 40 ml of ethyl acetate
12. customThe organic layer formed
13. customwas separated
14. washwashed successively with water
15. dry with materialan aqueous saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
16. customThe solvent was removed by distillation under reduced pressure
17. customthe residue thus obtained
18. stirringThe solution was stirred at 20° C. for 2 hours
19. customthe crystals thus separated
20. filtrationwere collected by filtration

ORD record

ord-c177865b4480417ebfefab2eab6c0ecb

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380878