Hydrochloric Acid → 2-[2-(N,N-diethylamino)ethoxy]-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol hydrochloride

A mixture of 0.61 g of 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol, 3 ml of 50% aqueous diethylamine solution, 0.45 mg of potassium iodide and 20 ml of ethanol is refluxed for three hours. Subsequently, 3 ml of 50% aqueous diethylamine solution is added to the thus refluxed reaction mixture, and the resulting reaction mixture is further refluxed for three hours. The solvent is removed from the thus refluxed mixture by distillation under reduced pressure. To the residue obtained are added 30 ml of ethyl acetate and 30 ml of water, after which the resulting mixture is adjusted to pH 1.5 with 6 N hydrochloric acid. Thereafter, the aqueous layer is separated and washed with 10 ml of ethyl acetate. 30 Milliliters of ethyl acetate is then added to the thus washed layer, after which the resulting mixture is adjusted to pH 10.5 with potassium carbonate. The organic layer is separated again, washed successively with 10 ml of water and 10 ml of a saturated saline solution, and then dried over anhydrous magnesium sulfate. The solvent is then removed from the thus dried layer by distillation under reduced pressure. The residue obtained is dissolved in 6 ml of ethanol. To the resulting solution are added 0.6 ml of 5 N dried hydrochloric acid-ethanol solution and 6 ml of diethyl ether. The mixture thus obtained is stirred at room temperature for one hour. The crystals precipitated are collected by filtration and washed with 2 ml of a liquid mixture of diethyl ether and ethanol (1:1) and then dried, to obtain 0.28 g of 2-[2-(N,N-diethylamino)-ethoxy]-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol hydrochloride.

1. temperatureis refluxed for three hours
2. customthe resulting reaction mixture
3. temperatureis further refluxed for three hours
4. customThe solvent is removed from the thus refluxed mixture by distillation under reduced pressure
5. customTo the residue obtained
6. customThereafter, the aqueous layer is separated
7. washwashed with 10 ml of ethyl acetate
8. addition30 Milliliters of ethyl acetate is then added to the thus washed layer
9. customThe organic layer is separated again
10. washwashed successively with 10 ml of water and 10 ml of a saturated saline solution
11. dry with materialdried over anhydrous magnesium sulfate
12. customThe solvent is then removed from the thus dried layer by distillation under reduced pressure
13. customThe residue obtained
14. customThe mixture thus obtained
15. customThe crystals precipitated
16. filtrationare collected by filtration
17. washwashed with 2 ml of a liquid mixture of diethyl ether and ethanol (1:1)
18. customdried

ORD record

ord-4efef6c161c446e6b9d032bd09047ff6

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05922721