N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyvinyl)indol-1-yl]acetamide → N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide

HRID 129681Notes

Reaction equation

HRID 129681 reaction equation
[CH3:1][N:2]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:3](=[O:29])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6]1.[H][H]>[Pd].C(O)C>[CH3:1][N:2]([CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:3](=[O:29])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6]1

Participants

5

Reactant 2

HCID 53736924N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyvinyl)indol-1-yl]acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 10505492N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.93 g of N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyvinyl)indol-1-yl]acetamide, 0.5 g of 10% palladium on activated carbon and 150 ml of ethanol is shaken under 40 psi of hydrogen on a Parr Apparatus for 40 minutes. The mixture is filtered to remove the catalysts and the filtrate is concentrated in vacuo. The residue is purified by dry column chromatography over silica gel eluting with a solvent system of ethyl acetate/hexane (2:1, v/v) to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide as white powder (m.p. 81°-83° C.).

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalysts
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is purified
  5. dry with materialby dry column chromatography over silica gel eluting with a solvent system of ethyl acetate/hexane (2:1

Sources & evidence

ORD record
ord-79b35697078846f5a455d05e1815e599
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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