Tetrahydrofuran → N-Propionylserotonin

HRID 324629

Reaktionsgleichung

Reaktionsgleichung von HRID 324629
[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.Cl.[O:15]1C[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)CC)(=O)CC>O>[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][C:16](=[O:15])[CH2:17][CH3:18]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 31263Propionic anhydrideHCID 160436Serotonin Hydrochloride

Produkt 1

HCID 594440N-PropionylserotoninAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of serotonin hydrochloride (10 g, 47.5 mmol.) in water (50 mL) were added, under argon atmosphere, tetrahydrofuran (20 mL) and a solution of sodium carbonate (5.3 g) in water (20 mL). The mixture was cooled to 0° C., to which was added propionic anhydride (6.2 g, 49.9 mmol.). The mixture was stirred for 2 hours at room temperature. The reaction mixture was subjected to extraction with ethyl acetate. The extract solution was washed with 1N HCl, a saturated aqueous solution of sodium hydrogencarbonate and water, which was dried and then concentrated to afford the title compound (yield 10.0 g, 98.0%) as an oily product. This compound was used, without refining further, for the subsequent reaction.

Aufarbeitung

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with 1N HCl
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, which was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cebb2af3cf244302b2006f585506baab
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218429B1

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