Hydrochloric Acid → 1-(Benzo[b]thiophen-5-yl)-2-(2-aminoethoxy)ethanol

Temperatur

85 °C

A mixture of 10 g of 2-(N-tritylamino)ethanol, 3.7 g of potassium tert-butoxide and 30 ml of dimethyl sulfoxide was heated to 85° C. Thereto was added a solution of 5.8 g of 2-(benzo[b]thiophen-5-yl)oxirane dissolved in 10 ml of dimethyl sulfoxide. The resulting mixture was stirred at the same temperature for 5 minutes. The reaction mixture was added to a mixture of 150 ml of ice water and 100 ml of ethyl acetate. The organic layer was separated. The aqueous layer was extracted with 30 ml of ethyl acetate. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 70 ml of a 50% aqueous formic acid solution and 30 ml of tetrahydrofuran. The resulting mixture was stirred at 50°-60° C. for 1 hours. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 50 ml of ethyl acetate and 30 ml of water. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The aqueous layer was separated. The organic layer was extracted twice each with 10 ml of water. The extracts were 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 to obtain 1.2 g of 1-(benzo[b]thiophen-5-yl)-2-(2-aminoethoxy) ethanol (compound No. 356.

1. customThe organic layer was separated
2. extractionThe aqueous layer was extracted with 30 ml of ethyl acetate
3. washThe combined organic layer was washed with water
4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
5. customThe solvent was removed by distillation under reduced pressure
6. customTo the residue thus obtained
7. stirringThe resulting mixture was stirred at 50°-60° C. for 1 hours
8. customThe solvent was removed by distillation under reduced pressure
9. customTo the residue thus obtained
10. customThe aqueous layer was separated
11. extractionThe organic layer was extracted twice each with 10 ml of water
12. additionTo the combined aqueous layer was added 50 ml of methylene chloride
13. customThe organic layer was separated
14. washwashed with water
15. dry with materialdried over anhydrous magnesium sulfate
16. customThe solvent was removed by distillation under reduced pressure

ORD-Eintrag

ord-5231daa4b1224fa2ae75fd0bdc464b98

Quelldatensatz

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05719150