Hydrochloric Acid → HCID 23336482, compound

HRID 903596Notes

Reaction equation

HRID 903596 reaction equation
[OH-].[Na+].CO.[CH2:5]([N:9]([C:21](=[O:29])[CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[CH:6]([CH3:8])[CH3:7].Cl>O>[CH2:5]([N:9]([C:21](=[O:29])[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[CH:6]([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 23336474HCID 23336474, compound

Product 1

HCID 23336482HCID 23336482, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1.5 ml of an aqueous 10% sodium hydroxide solution and 10 ml of a mixture of methanol and water (1:1) were added to 0.63 g of N-isobutyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-isobutyl-4-methoxycarbonylbutanamido)ethyl]-indole). The mixture was stirred at 60° C. for 30 minutes. After the reaction was completed, the mixture was evaporated to remove solvent. The residue thus obtained was adjusted to a pH of 2.0 with 10% hydrochloric acid, and then extracted with chloroform. The extract was washed with water and concentrated. 0.6 g of N-isobutyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-isobutyl-4-carboxybutanamido)ethyl]-indole) were thereby obtained. Yield: 99.3%

Workup

  1. customthe mixture was evaporated
  2. customto remove solvent
  3. customThe residue thus obtained
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0cdce937c989499ca9b9680aa93341a1
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

Loading…