Methylparaben → Benzoic acid, 4-[(1-methyl-4-piperidinyl)oxy]-, methyl ester

To a solution of 1-methyl-piperidin-4-ol (6.8 g. 59 mmoles), PPh3 (triphenylphosphine, 15.5 g, 59 mmoles) and 4-hydroxy-benzoic acid methyl ester (6 g, 39 mmoles) in THF (150 ml) at 0° C., diethyl azodicarboxylate (9.5 ml, 59 mmoles) in THF (30 ml) was slowly added. The reaction mixture was allowed to warm to room temperature over a period of 24 hours. It was then evaporated and the residue redissolved in 5% aqueous citric acid (700 ml). The solution was washed with ethyl acetate (3×250 ml), made alkaline with concentrated NH4OH (pH ˜8) and then extracted with dichloromethane (3×250 ml). The combined dichloromethane extracts were washed with brine, dried and evaporated to give an oil which was purified by flash chromatography on silica gel using dichloromethane-MeOH (90:10) as eluent, to give the title compound as a yellow oil (7.4 g, 75%).

1. customIt was then evaporated
2. dissolutionthe residue redissolved in 5% aqueous citric acid (700 ml)
3. washThe solution was washed with ethyl acetate (3×250 ml)
4. extractionextracted with dichloromethane (3×250 ml)
5. washThe combined dichloromethane extracts were washed with brine
6. customdried
7. customevaporated
8. customto give an oil which
9. customwas purified by flash chromatography on silica gel

ORD 기록

ord-249a99ebd60843cf95e29c0a1a1b97dd

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08557845B2