Methyltryptamine → N-methyl-N-(4-carboxybutyryl)-tryptamine

HRID 903594

Reaction equation

HRID 903594 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:14]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15]1>C1C=CC=CC=1>[CH3:1][N:2]([C:14](=[O:21])[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6088MethyltryptamineHCID 7940Glutaric anhydride

Product 1

HCID 23336462N-methyl-N-(4-carboxybutyryl)-tryptamineYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) were dissolved in 100 ml of benzene, and 5.7 g of glutaric acid anhydride were added thereto. The mixture was stirred at 80° C. for 3 hours. After the reaction was completed, the mixture was evaporated to remove solvent. 12.0 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole) were thereby obtained. Yield: 90%

Workup

  1. customthe mixture was evaporated
  2. customto remove solvent

Sources & evidence

ORD record
ord-6b474e5ee71e4eaa9c615e16d4c3b8f5
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Linked notes

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