1-Benzoylpiperidine-4-carbaldehyde → 4-(1-Hydroxy-prop-2-enyl)-1-benzoyl piperidine

HRID 1357936Notes

Reaction equation

HRID 1357936 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1>[OH:16][CH:15]([CH:12]1[CH2:13][CH2:14][N:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:10][CH2:11]1)[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 156812841-Benzoylpiperidine-4-carbaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 181875954-(1-Hydroxy-prop-2-enyl)-1-benzoyl piperidineYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 500 mg of 1-benzoylpiperidine-4-carboxaldehyde (Step C) in 10 mL THF at −78° C., was added 2.99 mmol of vinyl magnesium bromide. The solution was warmed to 0° C. and stirred for 1 h. The reaction was quenched with 15 mL of aq. ammonium chloride and extracted with 3×20 mL ether and the combined organic layers were dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography with 2:1 hexane:ethyl acetate followed by 1:1 hexane:ethyl acetate followed by hexane: ethyl acetate:methanol, 50:50:5 to give 411 mg of the title compound.

Workup

  1. customThe reaction was quenched with 15 mL of aq. ammonium chloride
  2. extractionextracted with 3×20 mL ether
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash chromatography with 2:1 hexane

Sources & evidence

ORD record
ord-759a76b11a724aa6a833e10609965b5c
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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