Sodium Carbonate → 1-(2-Naphthyl)-2-[(morpholin-2-yl)methoxy]ethanol

Temperature

50 °C

0.46 g of 1-(benzo[b]thiophen-5-yl)-2-(2-aminoethoxy) ethanol was dissolved in a mixture of 5 ml of water and 5 ml of dioxane. Thereto was added 0.21 g of sodium carbonate. The resulting mixture was heated to 50° C. Thereto was added 0.22 g of 2-chloropyrimidine. The resulting mixture was refluxed for 3 hours. The reaction mixture was added to a mixture of 30 ml of ice water and 30 ml of ethyl acetate. The organic layer was separated. The aqueous layer was extracted with 10 ml of ethyl acetate. The extract was combined with the previously separated organic layer. To the combined organic layer was added 20 ml of water and the resulting mixture was adjusted to pH 1.5 with 6N hydrochloric acid. The aqueous layer was separated. The organic layer was extracted with 10 ml of water. The extract was combined with the previously separated aqueous layer. To the combined aqueous layer was added 50 ml of methylene chloride and the resulting mixture was adjusted to pH 10.5 with potassium carbonate. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=20/1) to obtain an oily product. To the oily product were added 2 ml of ethanol and 70 mg of maleic acid. The resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 2 ml of diethyl ether. The resulting crystals were collected by filtration and dried to obtain 0.28 g of 1-(benzo[b]-thiophen-5-yl)-2-{[2-(pyrimidin-2-yl)amino]ethoxy}-ethanol 1/2 maleate (compound No. 359).

1. temperatureThe resulting mixture was refluxed for 3 hours
2. customThe organic layer was separated
3. extractionThe aqueous layer was extracted with 10 ml of ethyl acetate
4. additionTo the combined organic layer was added 20 ml of water
5. customThe aqueous layer was separated
6. extractionThe organic layer was extracted with 10 ml of water
7. additionTo the combined aqueous layer was added 50 ml of methylene chloride
8. customThe organic layer was separated
9. washwashed with water
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was removed by distillation under reduced pressure
12. customThe residue thus obtained
13. customwas purified by column chromatography (eluant: chloroform/ethanol=20/1)
14. customto obtain an oily product
15. filtrationThe resulting crystals were collected by filtration
16. customdried

ORD record

ord-a55e9fc38fd64eadb99ef21d05c89254

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719150