Methyl 4-pyridylacetate → HCID 24706329, compound

HRID 1389168Notes

Reaction equation

HRID 1389168 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10]C)=O)=[CH:3][CH:2]=1>C(N)CC>[CH2:2]([NH:1][C:8](=[O:10])[CH2:7][CH:4]1[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]1)[CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 122482Methyl 4-pyridylacetate

Product 1

HCID 24706329HCID 24706329, compound

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

Procedure

Methyl 2-(pyrid-4-yl)acetate (10 g.), n-propylamine (30 ml.) and 3 A molecular sieves (10 g.) were heated together at 100° for 148 hours in a stainless steel bomb. Excess amine and molecular sieves were removed and the crude product in glacial acetic acid (100 ml.) was hydrogenated over platinum oxide catalyst at 30°/50 p.s.i. until uptake of hydrogen ceased. The catalyst was removed by filtration, the excess acetic acid distilled off in vacuo, and the residue basified with aqueous sodium bicarbonate and extracted with ethyl acetate (100 ml.). The organic layer was dried (MgSO4) and evaporated in vacuo to give crude N-n-propyl-2-(piperid-4-yl) acetamide as an oil. This was utilized without further purification.

Workup

  1. customExcess amine and molecular sieves were removed
  2. customwas hydrogenated over platinum oxide catalyst at 30°
  3. customThe catalyst was removed by filtration
  4. distillationthe excess acetic acid distilled off in vacuo
  5. extractionextracted with ethyl acetate (100 ml.)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d97a1cca3488459390f62708be702873
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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