Reaktion #1866521

Reaktionsgleichung

product

Methyl 4-(1-piperazinyl)indole-2-carboxylate

potassium carbonate

triethylamine

potassium iodide

1-azepan-1-yl-4-chloro-2-phenylbutan-1-one

dihydrochloride

hydrogen chloride

→

4-[4-(4-Azepan- 1-yl-4-oxo-3-phenylbutyl)piperazin-1-yl]-1H-indole-2-carboxylic acid methyl ester

Lösungsmittel

dimethyl formamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted into ether (3×100 ml)
2. 2
   workup.ADDITIONtreated with excess dilute aqueous hydrogen chloride
3. 3
   FiltrationThe precipitate was filtered
4. 4
   Waschenwashed with ether (3×100 ml)
5. 5
   Extraktionextracted into ether (3×100 ml)
6. 6
   TrocknenThe extracts were dried (MgSO4)
7. 7
   Sonstigeevaporated in vacuo
8. 8
   Sonstigeto give a yellow crystalline glass
9. 9
   SonstigePurification by chromatography [alumina; ethyl acetate-hexane (2:3)]
10. 10
    Sonstigegave the product free base

Vorschrift

The product of Example 4 (1.30 g, 0.005 mol), 1-azepan-1-yl-4-chloro-2-phenylbutan-1-one (1.50 g, 0.005 mol), triethylamine (0.79 g, 0.0079 mol), and potassium iodide (0.2 g) were suspended in anhydrous dimethyl formamide (30 ml), stirred under argon for 3 h at 100° C., and poured into dilute potassium carbonate (300 ml). The mixture was extracted into ether (3×100 ml) and treated with excess dilute aqueous hydrogen chloride. The precipitate was filtered, washed with ether (3×100 ml), taken up into dilute sodium hydroxide solution (100 ml), and extracted into ether (3×100 ml). The extracts were dried (MgSO4), and evaporated in vacuo to give a yellow crystalline glass. Purification by chromatography [alumina; ethyl acetate-hexane (2:3)] gave the product free base. The dihydrochloride salt of the product (1.35 g) was precipated as a colourless solid by the addition of ethereal hydrogen chloride to a solution of the free base in ethyl acetate, m.p. 152°-168° C. (Found: C, 57.4; H, 7.45; N, 8.7. C30H38N4O3. 2HCl.3H2O requires C, 57.2; H, 7.4; N, 8.9%).

Quelle