HCID 19611639, compound → HCID 19611689, compound

HRID 1602412Notes

Reaction equation

HRID 1602412 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]>C(O)C.[Rh]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 19611639HCID 19611639, compound

Product 1

HCID 19611689HCID 19611689, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[3-(5-chloro-benzofuran-4-yl)-propyl]-acetamide (0.25 g) in ethanol (15 ml) was hydrogenated over 5% rhodium on carbon (80 mg) for 18 h. The catalyst was filtered off and the filtrate evaporated. The residue was purified by column chromatography on silica, eluting with dichloromethane/methanol 40:1 gave the title compound as a colourless solid (131 mg) mp 91-92

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was purified by column chromatography on silica
  4. washeluting with dichloromethane/methanol 40:1

Sources & evidence

ORD record
ord-95909df044774ac1ad0e6264f4733a3f
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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