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Hydrochloric Acid → HCID 20513191, Verbindung

HRID 1163908
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1163908
Cl.[CH2:2]([NH:9][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)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O[CH:24](OCC)[CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])C.Cl>CO.O>[CH2:30]([O:29][C:27]([NH:26][CH2:25][CH:24]1[C:13]2[NH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]=2[CH2:11][CH2:10][N:9]1[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 292521Benzyl 2,2-diethoxyethylcarbamateHCID 705330371H-Indole-3-ethanamine, N-(phenylmethyl)-, hydrochloride (1:1)

Produkt 1

HCID 20513191HCID 20513191, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 50 g of N-benzyl-tryptamine hydrochloride (i.e., 3-(2-(benzylamino)-ethyl)indole hydrochloride) in 500 ml of methanol-water (4:1) are added 57.9 g of N-benzyloxycarbonyl-aminoacetaldehyde diethylacetal and 25 ml of 10% hydrochloric acid, and the mixture is refluxed for 16 hours. After the reaction, the reaction mixture is evaporated under reduced pressure to remove solvent, and the resultant crystals are collected by filtration. After being washed with water and ether, said crystals are added to a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove solvent. The residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1)). 46 g of 1,2,3,4-tetrahydro-1-((N-benzyloxycarbonylamino)methyl)-2-benzyl-β-carboline are thereby obtained as a caramel. Yield: 62%

Aufarbeitung

  1. temperaturethe mixture is refluxed for 16 hours
  2. customAfter the reaction
  3. customthe reaction mixture is evaporated under reduced pressure
  4. customto remove solvent
  5. filtrationthe resultant crystals are collected by filtration
  6. washAfter being washed with water and ether
  7. additionare added to a saturated sodium bicarbonate solution
  8. extractionextracted with ethyl acetate
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove solvent
  13. customThe residue (oil, 60 g) is purified by silica gel chromatography (Solvent: chloroform-methanol (20:1))

Quellen und Nachweise

ORD-Eintrag
ord-ae08f53044ad42128a737c1846384b2b
Quelldatensatz
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04367230

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