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

HRID 1095500Notes

Reaction equation

HRID 1095500 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:1]2[C:16](=[O:17])[C:15]3[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]2=[O:18])=[CH:5]1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 6811Phthalic Anhydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tryptamine (3.04 g, 19.0 mmol) and phthalic anhydride (3.00 g, 20.0 mmol) were boiled for 12 h in a water separator. The solvent was distilled off i. vac. and the residue was dissolved in methylene chloride. Product was precipitated out by addition of cyclohexane and the precipitate was filtered off with suction and dried. Yield: 4.46 g (Ind-1; 87%)

Workup

  1. distillationThe solvent was distilled off i
  2. dissolutionand the residue was dissolved in methylene chloride
  3. customProduct was precipitated out by addition of cyclohexane
  4. filtrationthe precipitate was filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-0a5628519f784d81817ffed9b15b6109
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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