Acetic Anhydride → Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)-

HRID 741698Notes

Reaction equation

HRID 741698 reaction equation
[CH3:1][C:2]1[NH:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH2:6].[CH3:16][C:17](OC(C)=O)=[O:18]>C1COCC1>[CH3:1][C:2]1[NH:13][C:12]2[CH:11]=[CH:10][C:9]([O:14][CH3:15])=[CH:8][C:7]=2[C:3]=1[CH2:4][CH2:5][NH:6][C:17]([CH3:16])=[O:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 528992-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamine

Product 1

HCID 50279Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution in THF (15 mL) of the crude 2-methyl-5-methoxytryptamine, from the step above, TEA (0.7 mL) and 0.47 mL of Ac2O were added. The ice bath was removed and the solution stirred for 8 h. The solvent was evaporated in vacuo, the residue was taken up in ethyl acetate and washed with a saturated aqueous solution of NaHCO3 followed by saturated NaCl solution. The organic phase was dried (Na2SO4), concentrated under vacuum and the crude oil residue was purified by flash chromatography (silica gel; ethyl acetate-cyclohexane, 7:3) and crystallization. The overall yield of 4a was 0.541 g (44%); mp 122° C.; 1H NMR data were identical with that reported in literature (Flaugh et at., J. Med. Chem. 22, 63-67 (1979).

Workup

  1. customThe ice bath was removed
  2. customThe solvent was evaporated in vacuo
  3. washwashed with a saturated aqueous solution of NaHCO3
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customthe crude oil residue was purified by flash chromatography (silica gel; ethyl acetate-cyclohexane, 7:3) and crystallization

Sources & evidence

ORD record
ord-a6333ee5902e4b229167bc61ffbd9a34
Source dataset
uspto-grants-1996_09
Patent number
US05552428

Reaction notes

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