2-Oxoadipic acid → 1,2,3,4-Tetrahydro-1-carboxy-1-(3-carboxypropyl)-2-ethyl-beta-carboline

HRID 903604

Reaction equation

HRID 903604 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2].O=[C:16]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:17]([OH:19])=[O:18]>C1C=CC=CC=1.O1CCOCC1>[C:17]([C:16]1([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:7]2[NH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH2:5][CH2:4][N:3]1[CH2:1][CH3:2])([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 712-Oxoadipic acidHCID 6092N-Ethyltryptamine

Product 1

HCID 233365071,2,3,4-Tetrahydro-1-carboxy-1-(3-carboxypropyl)-2-ethyl-beta-carbolineYield 40%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

5 g of N-ethyl-tryptamine (i.e., 3-(2-ethylaminoethyl)-indole) were dissolved in 100 ml of absolute benzene, and a solution of 4.70 g of α-keto-adipic acid in 50 ml of absolute dioxane was added thereto at room temperature. The mixture was refluxed for 20 hours. After the reaction was completed, the mixture was evaporated to remove solvent. The residue thus obtained was recrystallized from ethanol, whereby 3.51 g of 1,2,3,4-tetrahydro-1-carboxy-1-(3-carboxypropyl)-2-ethyl-β-carboline were obtained. Yield: 38.0%

Workup

  1. customat room temperature
  2. temperatureThe mixture was refluxed for 20 hours
  3. customthe mixture was evaporated
  4. customto remove solvent
  5. customThe residue thus obtained
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-82daf5f83fa549d59bd1c96c58e2bfd8
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Linked notes

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