Formaldehyde → 1-[4-(p-Fluorophenyl)-4-hydroxy-2-butynyl]-4-(p-chlorophenyl)-4-hydroxypiperidine

Temperature

80 °C

To a solution of 4-(p-chlorophenyl)-4-hydroxypiperidine (4.00 g) in a mixture of dioxane (30 ml), water (10 ml), and 37 % formalin (2.06 g), there were added a solution of 3-(p-fluorophenyl)-3-hydroxy-1-propyne (2.38 g) in dioxane (5 ml) and a solution of cupric sulfate pentahydrate (127 mg) in water (4 ml) under ice-cooling. The resulting mixture was heated at 80° C for 2 hours and, after cooling, the resulting mixture was filtered and the filtrate was concentrated under reduced pressure and extracted with chloroform. The chloroform extracts were dried over magnesium sulfate. After evaporation of the solvent, the residual oil was chromatographed on silica gel to afford 1-[4-(p-fluorophenyl)-4-hydroxy-2-butynyl]-4-(p-chlorophenyl)-4-hydroxypiperidine (4.56 g) as white crystals, M.P. 145° - 146.2° C.

1. temperatureafter cooling
2. filtrationthe resulting mixture was filtered
3. concentrationthe filtrate was concentrated under reduced pressure
4. extractionextracted with chloroform
5. dry with materialThe chloroform extracts were dried over magnesium sulfate
6. customAfter evaporation of the solvent
7. customthe residual oil was chromatographed on silica gel

ORD record

ord-47faf86cc8014f3d8c710ff54681a8c2

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04012515