Hydrochloric Acid → 6-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-phenylheptanamide, monohydrochloride hydrate

HRID 273810

Reaktionsgleichung

Reaktionsgleichung von HRID 273810
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.[ClH:14].[C:15]1([NH:21][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=O)[CH3:28])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+].Cl>CO.O.C(O)C>[OH2:7].[ClH:14].[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][CH:27]([CH3:28])[CH2:26][CH2:25][CH2:24][CH2:23][C:22]([NH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:30]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 160436Serotonin HydrochlorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 19422086N-phenyl-6-oxo-heptanamide

Produkt 1

HCID 1317177876-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-phenylheptanamide, monohydrochloride hydrateAusbeute 176,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Serotonin hydrochloride (1.000 g) and N-phenyl-6-oxo-heptanamide (1.289 g) were stirred in methanol (47 mL) under a nitrogen atmosphere and treated with sodium cyanoborohydride (0.444 g), excluding light from the reaction. After 4 d at ca. 23° C., a solution of sodium bicarbonate (1.00 g) in water (25 mL) was added. One hour later, the reaction was diluted with water (75 mL) and extracted with 1:4 2-propanol:dichloromethane (3×75 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a foaming oil which was chromatographed using 5:20:80 triethylamine:ethanol:ethyl acetate, isolating the component with an Rf of 0.3. The resulting oil was twice reconcentrated in vacuo from ethanol (100 mL) and then redissolved in ethanol (100 mL). This solution was treated with 1:9 concentrated hydrochloric acid: ethanol (6 mL), concentrated in vacuo reconcentrated from ethanol (100 mL) to an oil, and the oil placed under vacuum to yield the title compound as a solid (1.80 g).

Aufarbeitung

  1. customfrom the reaction
  2. extractionextracted with 1:4 2-propanol
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a foaming oil which
  6. customwas chromatographed
  7. customethanol:ethyl acetate, isolating the component with an Rf of 0.3
  8. concentrationethanol (6 mL), concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77e8716395f14d96a5690461ff37d335
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387604

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