Potassium Hydroxide → N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carboxyethyl)indol-1-yl]acetamide

HRID 129682Notes

Reaction equation

HRID 129682 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]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:6]1.[OH-].[K+]>C(O)C.O>[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]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:6]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10505492N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide

Product 1

HCID 10838099N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carboxyethyl)indol-1-yl]acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 0.7 g (1.4 mmol) of N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide in 20 ml of ethanol is added a solution of 0.2 g of potassium hydroxide in 3 ml of water. The mixture is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is dissolved in water and the resulting solution adjusted to pH 4 with 1N aqueous HCl solution. The precipitate which forms is extracted into ethyl acetate. The organic solution is washed with brine, dried over magnesium sulfate and concentrated in vacuo to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carboxyethyl)indol-1-yl]acetamide as a beige powder (m.p. 122°-125° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in water
  3. extractionThe precipitate which forms is extracted into ethyl acetate
  4. washThe organic solution is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ef4269bb7d74a5996894ba02f30b977
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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