Dimethylformamide → 2-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane

A mixture of 7.5 g of 1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)-2-[2-(p-toluenesulfonyloxy) -ethoxy]ethane, 2.65 ml of N-methylpiperazine, 3.96 g of potassium carbonate and 38 ml of N,N-dimethylformamide was stirred for 2 hours at 90°-100° C. The reaction mixture was cooled and added to a mixture of 100 ml of diethyl ether and 100 ml of ice water. The organic layer was separated. The aqueous layer was extracted twice each with 25 ml of diethyl ether. The extracts were 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. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=10/1) to obtain 3.36 g of colorless, oily 2-[2-(4-methylpiperazin-1-yl)ethoxy] -1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane (compound No. 258).

1. temperatureThe reaction mixture was cooled
2. customThe organic layer was separated
3. extractionThe aqueous layer was extracted twice each with 25 ml of diethyl ether
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. customThe residue thus obtained
8. customwas purified by column chromatography (eluant: chloroform/ethanol=10/1)

ORD 기록

ord-d5601551196d433fa5008fbb7cf8a406

출처 데이터셋

uspto-grants-1994_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05280032