Hydrochloric Acid → HCID 23336498, compound

HRID 903598Notes

Reaction equation

HRID 903598 reaction equation
Cl.C([O:4][C:5]([CH:7](C(OCC)=O)[CH2:8][CH2:9][CH:10]1[C:22]2[NH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH2:13][CH2:12][N:11]1[CH2:23][CH3:24])=[O:6])C>C(O)(=O)C>[C:5]([CH2:7][CH2:8][CH2:9][CH:10]1[C:22]2[NH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH2:13][CH2:12][N:11]1[CH2:23][CH3:24])([OH:6])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23336464HCID 23336464, compound

Product 1

HCID 23336498HCID 23336498, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

3.0 ml of acetic acid and 1.5 ml of conc. hydrochloric acid were added to 0.70 g of 1,2,3,4-tetrahydro-1-[3,3-bis(ethoxycarbonyl)propyl]-2-ethyl-β-carboline. The mixture was stirred at 120° C. for 5 hours. After the reaction was completed, the mixture was evaporated to remove solvent, whereby 1,2,3,4-tetrahydro-1-(3-carboxypropyl)-2-ethyl-β-carboline was obtained as a crude product. 30 ml of 10% methanolic hydrogen chloride were added to the crude product, and the mixture was refluxed for 2 hours. After the reaction was completed, the mixture was concentrated. The residue thus obtained was alkalified with an aqueous saturated sodium bicarbonate solution under cooling, and extracted with ethyl acetate. The extract was washed with water, dried and evaporated to remove solvent. The residue thus obtained was purified by silica gel chromatography (Solvent: chloroform-methanol (20:1)), whereby 470 mg of 1,2,3,4-tetrahydro-1-(3-methoxycarbonylpropyl)-2-ethyl-β-carboline were obtained. Yield: 84.0%

Workup

  1. customthe mixture was evaporated
  2. customto remove solvent

Sources & evidence

ORD record
ord-fe8d4d8ee9c94d6ebe1a434b74c1eb8f
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

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