Vanillin → Methyl 1-(prop-2-yn-1-yl)piperidine-4-carboxylate

HRID 2102271Notes

Reaction equation

HRID 2102271 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.[CH2:11](Br)[C:12]#[CH:13].O=CC1C=CC(O)=C(OC)C=1>ClCCl>[CH3:8][O:7][C:5]([CH:4]1[CH2:9][CH2:10][N:1]([CH2:13][C:12]#[CH:11])[CH2:2][CH2:3]1)=[O:6]

Participants

5

Reactant 3

HCID 1183Vanillin2×HCID 7842Propargyl bromideHCID 424914Methyl isonipecotate

Product 1

HCID 58860514Methyl 1-(prop-2-yn-1-yl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl isonipecotate 3.5 g (24.4 mmol, 3.30 mL) in 100 mL dichloromethane was added TEA (1.5 eq, 36.6 mmol, 5.1 mL), propargyl bromide (3.0 eq, 73.2 mmol, 6.5 ml), at room temperature for 36 hrs. The reaction was quenched with 35 mL water to yield to provide a clear solution. The solution was extracted with dichloromethane 2×25 mL, dried with Na2SO4, and the solvent evaporated to provide a yellow oil. r.f. (40% EtOAc/Hexanes) 0.26 stains faint white with Vanillin, starting material r.f. 0.05 stains yellow with Vanillin. The product appeared pure after extraction.

Workup

  1. customThe reaction was quenched with 35 mL water
  2. customto yield
  3. customto provide a clear solution
  4. extractionThe solution was extracted with dichloromethane 2×25 mL
  5. dry with materialdried with Na2SO4
  6. customthe solvent evaporated
  7. customto provide a yellow oil
  8. extractionafter extraction

Sources & evidence

ORD record
ord-564f4a6d97f14bab8dd7109ff2d1c620
Source dataset
uspto-grants-2009_08
Patent number
US07576069B2

Reaction notes

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