Reaktion #1866520

Reaktionsgleichung

potassium carbonate

product

Methyl 4-aminoindole-2-carboxylate

bis(2-chloroethyl)amine hydrochloride

potassium carbonate

bis(2- chloroethyl)amine hydrochloride

potassium carbonate

→

product

Ausbeute 37.8%

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

Ausbeute 37.8%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter another 6 h
2. 2
   Extraktionextracted with ether (3×300 ml) and ethyl acetate (2×250 ml)
3. 3
   Trocknendried (MgSO4)
4. 4
   Waschenwashed with water (2×200 ml)
5. 5
   SonstigeEvaporation of the solvent in vacuo
6. 6
   Sonstigegave a solid which
7. 7
   Sonstigewas recrystallised from ether

Vorschrift

A mixture of the product of Example 3 (9.5 g, 0.051 mol), bis(2-chloroethyl)amine hydrochloride (10.6 g, 0.06 mol), and potassium carbonate (8.3 g, 0.06 mol) in anhydrous dimethylformamide (30 ml) was heated at 110° C. under argon. Further addition of bis(2- chloroethyl)amine hydrochloride (5.5 g. 0.031 mol) and potassium carbonate (4.2 g, 0.031 mol) were made after 7 h and 16 h. After another 6 h,the reaction mixture was poured into dilute potassium carbonate solution (400 ml) and extracted with ether (3×300 ml) and ethyl acetate (2×250 ml). The extracts were combined, dried (MgSO4), and washed with water (2×200 ml). Evaporation of the solvent in vacuo gave a solid which was recrystallised from ether to give the product (5.0 g) as off-white crystals, m.p. 177°-180° C.

Quelle