Pyridine → N-(6-Methyl-1H-indol-3-ylmethyl)-acetamide

HRID 646065Notes

Reaction equation

HRID 646065 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][NH2:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 28806263(6-methyl-1H-indol-3-yl)methanamine

Product 1

HCID 68580773N-(6-Methyl-1H-indol-3-ylmethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C-(6-methyl-1H-indol-3-yl)-methylamine (0.24 g) in dichloromethane (4 ml) was added acetic anhydride (0.14 ml) and pyridine (0.13 ml) and stirring was continued at 22° C. for 20 min. The mixture was washed with aqueous HCl (1N), the organic layer was dried and evaporated. The residue was chromatographed on silica using dichloromethane/methanol (70:1) to give N-(6-methyl-1H-indol-3-ylmethyl)-acetamide as colorless foam (0.15 g). MS: 203.1 ([M+H]+).

Workup

  1. washThe mixture was washed with aqueous HCl (1N)
  2. customthe organic layer was dried
  3. customevaporated
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-073e0a2bf14f44648ed167d27b5d2aac
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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