Methane → Ethyl 2-(piperidin-4-yloxy)acetate

HRID 329028Notes

Reaction equation

HRID 329028 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].C>C(O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 297MethaneHCID 20295373N-Benzyl-4-(carbethoxymethoxy)-piperidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11263922Ethyl 2-(piperidin-4-yloxy)acetateYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 36.4 g (0.131 mole) of ethyl 2-(1-benzyl-4-piperidyloxy)-acetate in 200 ml of absolute ethanol was reacted with hydrogen at 50° C in the presence of 3.5 g of 5% palladized charcoal until the theoretical amount of hydrogen was absorbed and the catalyst was filtered off. The ethanol was evaporated off and the residue was distilled to obtain 18.2 g (74% yield) of ethyl 2-(4-piperidyloxy)-acetate as a clear oil boiling at 102° C at 0.1 mm Hg and having a refractive index nD20 = 1.4665.

Workup

  1. customwas absorbed
  2. filtrationthe catalyst was filtered off
  3. customThe ethanol was evaporated off
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-11158ffed11a48318cf797a9a34c58bc
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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