1,4-Dioxane → N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide

HRID 129688Notes

Reaction equation

HRID 129688 reaction equation
[CH3:1][N:2]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1.[OH-:31].C([N+](C)(C)C)[C:33]1[CH:38]=[CH:37]C=CC=1.C1C=CC(C2C=CC(NC3C=CC=CC=3)=CC=2)=CC=1.[O:62]1CCO[CH2:64][CH2:63]1>>[CH3:1][N:2]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[N:7]([CH:37]=[CH:38][C:33]([O:62][CH2:63][CH3:64])=[O:31])[CH:6]=1

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 13087229N-phenyl-(1,1'-biphenyl)-4-amineHCID 19372283N-methyl-N-phenethyl-2-(5-benzyloxyindol-3-yl)acetamide

Product 1

HCID 54482929N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide

Procedure

To a mixture of 1.579 g (3.96 mmol) of N-methyl-N-phenethyl-2-(5-benzyloxyindol-3-yl)acetamide and 0.4 ml of benzyltrimethylammonium hydroxide (40% solution in methanol) in 15 ml of dioxane is added with stirring 0.44 ml (0.43 g, 4.35 mmol) of ethyl propriolate. A reddish solution is obtained, which is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is taken up in ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by dry column chromatography over silica gel eluting with a solvent system of 5% ethyl acetate in methylene chloride to yield 450 mg of N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide.

Workup

  1. additionis added
  2. customA reddish solution is obtained
  3. concentrationconcentrated in vacuo
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified
  8. dry with materialby dry column chromatography over silica gel eluting with a solvent system of 5% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-5d5e73cb61e64b33ad77920a61d0ab71
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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