Methanol → 4-[4-[4-[4-(4-methoxybutoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester

Temperature

0 °C

To a solution of 4-[4-[4-hydroxy-4-[4-(4-methoxybutoxy)phenyl]piperidin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester (3.41 g) in dichloromethane (50 ml) was added trifluoroacetic acid (8.5 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for further 6 hours. To the reaction mixture was added 1 mol/ml sodium hydroxide solution (170 ml), dichloromethane (136 ml) and methanol (14 ml). The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution) to give 4-[4-[4-[4-(4-methoxybutoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester (2.23 g).

1. washThe organic layer was washed with water and brine
2. dry with materialdried over magnesium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution)

ORD record

ord-63a186bd99bf4cb3b2d8f7fcccda0912

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884868B1