Acetone → 1-[4-(p-Fluorophenyl)-4-hydroxy-2-butenyl]-4-(p-chlorophenyl)-4-hydroxypiperidine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:32])[C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([OH:24])[CH2:20][CH2:19]2)=[CH:10][CH:9]=1.CC(C)=O>CCOCC>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([OH:32])[CH:15]=[CH:16][CH2:17][N:18]2[CH2:19][CH2:20][C:21]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([OH:24])[CH2:22][CH2:23]2)=[CH:12][CH:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To an ethereal solution (14 ml) of lithium aluminum hydride (0.37 g) was added a solution of 1-[4-(p-fluorophenyl)-4-hydroxy-2-butynyl]-4-(p-chlorophenyl)-4-hydroxypiperidine (1.20 g) in ether (13 ml) under ice-cooling. After stirring at 10° C for 1.5 hours and further at 25° C for 4 hours, acetone was added thereto in order to consume excess of lithium aluminum hydride. The resulting mixture was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated to afford 1-[4-(p-fluorophenyl)-4-hydroxy-2-butenyl]-4-(p-chlorophenyl)-4-hydroxypiperidine (1.50 g) as white needles, M.P. 149° - 151° C.
Workup
- temperaturecooling
- customin order to consume excess of lithium aluminum hydride
- additionThe resulting mixture was poured into an aqueous ammonium chloride solution
- extractionextracted with ethyl acetate
- washThe ethyl acetate extracts were washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2a182c0a3181448c955cfcd64ba5e69e
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04012515
Reaction notes
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