Allyl bromide → HCID 12725716, compound

HRID 2081885Notes

Reaction equation

HRID 2081885 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](Br)[CH:15]=[CH2:16]>C(O)C>[CH2:16]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 12725716HCID 12725716, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a mixture of 4-hydroxypiperidine (75 g, 0.74 mol) and potassium carbonate (104 g, 0.75 mol) in ethanol (250 ml) is added allyl bromide (65 ml, 0.74 mol) in four equal portions over a three-hour period. After the addition is complete, the reaction mixture is stirred at ambient temperature until the disappearance of the reactants, as determined by TLC analysis (approximately six hours). The insoluble solids formed are then removed by filtration and the filtrate is concentrated in vacuo. The residue is purified by flash chromatography on silica gel with a mixture of 25% (vol.) methanol in ethyl acetate as the solvent to give 53.2 g (51% yield) of the title compound as a yellow oil.

Workup

  1. additionAfter the addition
  2. customas determined by TLC analysis (approximately six hours)
  3. customThe insoluble solids formed
  4. customare then removed by filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by flash chromatography on silica gel with a mixture of 25% (vol.) methanol in ethyl acetate as the solvent

Sources & evidence

ORD record
ord-1981fae5d629470c932293141260181c
Source dataset
uspto-grants-1993_02
Patent number
US05185448

Reaction notes

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