Bis(1,3-dichloroisopropyl ether) → 4-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]benzaldehyde

To a solution of 1-(4-methylphenylsulfonyl)-4-phenylpiperidine (1.0 g) and 1,1-dichloromethylmethylether (0.57 ml) in dichloromethane (5 ml) was added at 0° C. a solution of titanium tetrachloride (0.7 ml) in dichloromethane (5 ml), and the mixture was stirred at room temperature for 2 hours. The mixture was added to stirred ice/water to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution and saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2) to give pale yellow crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]benzaldehyde (0.381 g). (469.4 mg of the starting materials were collected)

1. additionThe mixture was added
2. customthe reaction
3. extractionThe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with sodium bicarbonate solution and saturated brine
5. dry with materialdried with magnesium sulfate
6. concentrationUnder reduced pressure, the mixture was concentrated
7. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2)

ORD-Eintrag

ord-35a49dfd4eef4eb59e0909da870a2bee

Quelldatensatz

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06172061B2