p-Toluenesulfonic acid → N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine

HRID 903597Notes

Reaction equation

HRID 903597 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1>CO>[CH3:12][N:13]([C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:1])=[O:30])[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 23336462N-methyl-N-(4-carboxybutyryl)-tryptamine

Product 1

HCID 23336480N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamineYield 16,231%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 ml of methanol and 10 mg of p-toluenesulfonic acid were added to 2.88 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole). The mixture was refluxed for 5 hours. After the reaction was completed, the mixture was concentrated to about 10 ml. The concentrated mixture was diluted with an aqueous saturated sodium bicarbonate solution under cooling and then extracted with ethyl acetate. The extract was washed with water, dried and then concentrated to dryness. The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane. 2.85 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]-indole) were thereby obtained. M.p. 101°-102° C. Yield: 95%

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. concentrationthe mixture was concentrated to about 10 ml
  3. additionThe concentrated mixture was diluted with an aqueous saturated sodium bicarbonate solution
  4. temperatureunder cooling
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue thus obtained
  10. customwas recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-6091593c3b1b4973a408cd8778348164
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

Loading…