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

HRID 1292372Notes

Reaction equation

HRID 1292372 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 on silica gel (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 on silica gel (methylene chloride:methanol, 97:3)

Sources & evidence

ORD record
ord-2b24cd168c48401994b1059af440da32
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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