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

HRID 254145Notes

Reaction equation

HRID 254145 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-35c45820b8e94249a0a3c83cb3a3f31c
Source dataset
uspto-grants-2011_01
Patent number
US07875595B2

Reaction notes

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