Tryptamine → 1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,5-dione

HRID 1095527Notes

Reaction equation

HRID 1095527 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH2:3][CH2:2]1.[NH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.C([O-])(=O)C.[K+]>C(O)(=O)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:10][CH2:9][N:8]2[C:4](=[O:5])[CH2:3][CH2:2][C:1]2=[O:7])=[CH:12]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 7922Succinic anhydrideHCID 517044Potassium Acetate

Product 1

HCID 7885801-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Succinic anhydride (2.27 g, 22.7 mmol) was added in portions to a hot solution of tryptamine (3.30 g, 20.6 mmol) and potassium acetate (2.23 g, 22.7 mmol) in acetic acid (10 ml). The reaction solution was heated at the boiling point for 3 h and subsequently stirred at RT overnight and the precipitate which had precipitated out was filtered off and washed with acetic acid and EtOH. Yield: 3.00 g (Ind-61, 60%)

Workup

  1. temperatureThe reaction solution was heated at the boiling point for 3 h
  2. customthe precipitate which had precipitated out
  3. filtrationwas filtered off
  4. washwashed with acetic acid and EtOH

Sources & evidence

ORD record
ord-c3d70bbf4e2d437cb67882dc191be46b
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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