Allyl bromide → 1-(2-Propenyl)piperidine

HRID 1817836Notes

Reaction equation

HRID 1817836 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7](Br)[CH:8]=[CH2:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:9]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:8]=[CH2:7]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 8082PiperidineHCID 11430Potassium Carbonate

Product 1

HCID 1397561-(2-Propenyl)piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The piperidine from Example 114 (56 mg, 0.15 mmol) was dissolved in dimethylformamide (2 mL) and was treated with allyl bromide (17 μL, 0.18 mmol), and potassium carbonate (63 mg, 0.45 mmol) and the mixture was stirred at r.t. for 4 hrs. The mixture was diluted with water (2 mL) and the solution washed with ethyl acetate (3×10 mL). The organic phase was dried (MgSO4) and evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes to give the N-allylpiperidine. 1H NMR (CDCl3) 7.42-7.37 (4H, m), 7.13-7.02 (2H, m), 6.90-6.83 (1H, m), 5.83-5.71 (1H, m), 5.12-5.08 (2H, m), 2.99-2.95 (2H, m), 2.86 (2H, d, J=6.5 Hz), 2.84-2.38 (4H, m), and 1.91-1.85 (2H, m); MS MH+=412(414).

Workup

  1. washthe solution washed with ethyl acetate (3×10 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give a pale oil which
  5. customwas purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1aeb061beff449dfa6b13f1e2ca63a50
Source dataset
uspto-grants-2009_10
Patent number
US07598386B2

Reaction notes

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