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

HRID 1068240Notes

Reaction equation

HRID 1068240 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]>>[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

3

Reactant 2

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

To a solution of 500 mg of 1-benzoyl-piperidine-4-carboxaldehyde (step C) in 10 ml TBF at −78° C., was added 2.99 mmol of vinyl magnesium bromide. The solution was warmed to 0° C. and stirred for 1 hour. The reaction was quenched with 15 mL of aq. NH4Cl and extracted with 3×20 ml Et2O and the combined organic layers were dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography with 2:1 hexane:EtOAc followed by 1:1 hexane:EtOAc followed by hexane:EtOAc:MeOH, 50:50:5 to give 411 mg of the title compound. 1H NMR (500 MHz) 1.31 (m, 2H), 1.74 (m, 5H), 2.69 (m, 1H), 2.92 (m, 1H), 4.80 (m, 1H), 3.68 (m, 1H), 5.22 (dd, 2H), 5.84 (m, 1H), 7.43 (m, 5H).

Workup

  1. customThe reaction was quenched with 15 mL of aq. NH4Cl
  2. extractionextracted with 3×20 ml Et2O
  3. dry with materialthe combined organic layers were dried over MgSO4
  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-8fd94d96b85741df9490c800c0fc42e2
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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