HCID 53876544, compound → HCID 20498725, compound

HRID 2166694Notes

Reaction equation

HRID 2166694 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][C:8]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)[CH3:3]>C(O)C.[Pd]>[CH3:1][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)[CH3:3]

Participants

4

Reactant 1

HCID 53876544HCID 53876544, compound

Product 1

HCID 20498725HCID 20498725, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(5-dimethylaminomethyl-2-thienyl)acrylate (30.30 g) in ethanol (175 ml) was hydrogenated (initial press. 344 kPa) over a total of 8.5 hr at a temperature of between 55°-60° C. in the presence of 10% palladium on charcoal catalyst (ca. 10 g) used in two portions. The first portion was added to the reaction mixture initially and the second after 5.5 hrs. The catalyst was filtered off over diatomecous earth and washed with ethanol. The filtrate was evaporated at reduced pressure to give ethyl 3-(5-dimethylaminomethyl-2-thienyl)-propionate (29.91 g) as a colourless oil.

Workup

  1. customover a total of 8.5 hr
  2. customof between 55°-60° C.
  3. additionThe first portion was added to the reaction mixture initially
  4. filtrationThe catalyst was filtered off over diatomecous earth
  5. washwashed with ethanol
  6. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-c2ca21390ac64286a3d380c0d750afe3
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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