Sodium hydride → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(acetylthio)acetamide

A solution of 0.47 ml of thioacetic acid in 20 ml of tetrahydrofuran was added dropwise, whilst ice-cooling and in an atmosphere of nitrogen, to a suspension of 0.29 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 20 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 2.00 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-chloroacetamide [prepared as described in step (a) above] in 20 ml of tetrahydrofuran was added dropwise to the mixture, whilst ice-cooling, after which it was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, the residue was mixed with water, and the resulting aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and ethyl acetate as the eluent, to give 1.72 g (yield 77%) of the title compound as an oil.

1. temperaturecooling
2. stirringafter which it was stirred at room temperature for 30 minutes
3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
4. additionthe residue was mixed with water
5. extractionthe resulting aqueous mixture was extracted with ethyl acetate
6. concentrationThe extract was concentrated by evaporation under reduced pressure
7. customthe concentrate was purified by column chromatography through silica gel
8. additionby volume mixture of methanol and ethyl acetate as the eluent

ORDレコード

ord-c107a231c7d24ba6b3600e358636d93f

出典データセット

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05616579