Tryptamine → 2-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dione

HRID 1458332Notes

Reaction equation

HRID 1458332 reaction equation
[C:1]([N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])(OCC)=O.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26]CN)=[CH:18]1>>[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][CH2:1][N:6]2[C:7](=[O:16])[C:8]3[C:9](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:11])=[CH:18]1

Participants

3

Reactant 2

HCID 1150TryptamineHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 2885772-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dioneYield 85.5%

Procedure

To a stirred suspension of 2-(1H-indol-3-yl)ethylamine (2.0 g in 20 mL of dry tetrahydrofuran) was added N-carbethoxyphthalimide (2.85 g) and the mixture heated to reflux on an oil bath. After 48 hours the reaction was cooled to room temperature, filtered and the filtrate concentrated in vacuo. The resulting solid was suspended in a mixture of hexane/methylene chloride (2.5:1) and filtered. Purification of the collected solids by flash chromatography (methylene chloride:methanol, 97:3) gave the title compound (3.1 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe resulting solid was suspended in a mixture of hexane/methylene chloride (2.5:1)
  6. filtrationfiltered
  7. customPurification of the collected solids by flash chromatography (methylene chloride:methanol, 97:3)

Sources & evidence

ORD record
ord-81f20e1192d147c69bdb3bbf3d359482
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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