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Acetone → 1-[4-(p-Fluorophenyl)-4-hydroxy-2-butenyl]-4-(p-chlorophenyl)-4-hydroxypiperidine

HRID 596948
Notes
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Reaction equation

HRID 596948 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 180AcetoneHCID 132773661-[4-(p-Fluorophenyl)-4-hydroxy-2-butynyl]-4-(p-chlorophenyl)-4-hydroxypiperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 536616361-[4-(p-Fluorophenyl)-4-hydroxy-2-butenyl]-4-(p-chlorophenyl)-4-hydroxypiperidineYield 124.3%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

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

  1. temperaturecooling
  2. customin order to consume excess of lithium aluminum hydride
  3. additionThe resulting mixture was poured into an aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2a182c0a3181448c955cfcd64ba5e69e
Source dataset
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04012515

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes