Hydrochloric Acid → 2-(2-Aminoethoxy)-1-(1-naphthyl)ethanol

Temperature

85 °C

A mixture of 3.5 g of potassium tert-butoxide, 9.4 g of N-tritylethanolamine and 50 ml of dimethyl sulfoxide was heated to 85° C. Thereto was added 5.3 g of 2-(1-naphthyl)oxirane. The resulting mixture was stirred at the same temperature for 5 minutes. The reaction mixture was cooled and added to a mixture of 100 ml of ethyl acetate and 150 ml of ice water. The organic layer was separated. The aqueous layer was extracted with 50 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 80 ml of a 50% aqueous formic acid solution and 40 ml of tetrahydrofuran. The resulting mixture was stirred at 50°-60° C. for 1 hour. The reaction mixture was cooled. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 60 ml of ethyl acetate and 60 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 15 ml of water. The extracts were combined with the previously separated aqueous layer. To the combined aqueous layer was added 100 ml of chloroform 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 the residue thus obtained was added 10 ml of diisopropyl ether. The resulting crystals were collected by filtration and dried to obtain 1.8 g of 2-(2-aminoethoxy)-1-(1-naphthyl)ethanol (compound No. 267).

1. temperatureThe reaction mixture was cooled
2. customThe organic layer was separated
3. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
4. washThe combined organic layer was washed with water
5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
6. customThe solvent was removed by distillation under reduced pressure
7. customTo the residue thus obtained
8. stirringThe resulting mixture was stirred at 50°-60° C. for 1 hour
9. temperatureThe reaction mixture was cooled
10. customThe solvent was removed by distillation under reduced pressure
11. customTo the residue thus obtained
12. customThe aqueous layer was separated
13. extractionThe organic layer was extracted twice each with 15 ml of water
14. additionTo the combined aqueous layer was added 100 ml of chloroform
15. customThe organic layer was separated
16. washwashed with water
17. dry with materialdried over anhydrous magnesium sulfate
18. customThe solvent was removed by distillation under reduced pressure
19. customTo the residue thus obtained
20. filtrationThe resulting crystals were collected by filtration
21. customdried

ORD record

ord-e38c0c9cadc746b78ca6f33e8498eb60

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05872117