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

HRID 596947Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:15]=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([OH:27])[C:25]#[CH:26])=[CH:20][CH:19]=1>O1CCOCC1.O>[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]([OH:27])[C:25]#[C:26][CH2:15][N:11]2[CH2:10][CH2:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([OH:14])[CH2:13][CH2:12]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-47faf86cc8014f3d8c710ff54681a8c2
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04012515

Reaction notes

Loading…