Methyltryptamine → 3-[2-(N-(4-carboxy-4,4-dimethyl-1-oxobutyl)-N-methylamino)-ethyl]-indole

HRID 2295489Notes

Reaction equation

HRID 2295489 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.[CH3:14][C:15]1([CH3:23])[CH2:21][CH2:20][C:19](=[O:22])[O:18][C:16]1=[O:17]>C1C=CC=CC=1>[C:16]([C:15]([CH3:23])([CH3:14])[CH2:21][CH2:20][C:19]([N: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)[CH3:1])=[O:22])([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 6088MethyltryptamineHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

Product 1

HCID 155908293-[2-(N-(4-carboxy-4,4-dimethyl-1-oxobutyl)-N-methylamino)-ethyl]-indole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.97 g of 3-(2-methylaminoethyl)-indole, 100 ml of dry benzene and 5.69 g of 2,2-dimethylglutaric anhydride are introduced at ambient temperature into a 250 ml round-bottomed flask provided with a condenser, a CaCl2 drying tube and a magnetic stirrer. The reaction mixture is heated slowly at the reflux temperature for 1 hour 30 minutes with stirring. It is then left to cool and to stand overnight at ambient temperature.

Workup

  1. customprovided with a condenser, a CaCl2 drying tube and a magnetic stirrer
  2. temperatureThe reaction mixture is heated slowly at the reflux temperature for 1 hour 30 minutes
  3. waitIt is then left
  4. temperatureto cool

Sources & evidence

ORD record
ord-13371c727eb946e4b660e6a787445d09
Source dataset
uspto-grants-1984_01
Patent number
US04425351

Reaction notes

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