Reaktion #63336

Reaktionsgleichung

sodium borohydride

1,2,3,6-tetrahydropyridine

N'-cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2 -(phenylmethylene) hydrazinecarboximidamide

hydrochloric acid

→

title compound

1-Methyl-N5 -[3-[3-[1-(1,2,3,6-tetrahydropyridinyl)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

Lösungsmittel

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for 18 h
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe filtrate evaporated in vacuo
4. 4
   SonstigeThe resulting oil was partitioned between ethyl acetate water
5. 5
   SonstigeThe organic phase was evaporated in vacuo
6. 6
   Sonstigethe residue was purified by column chromatography on silica
7. 7
   SonstigeEvaporation of the eluates

Vorschrift

A solution of N'-cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2 -(phenylmethylene) hydrazinecarboximidamide (2.62 g) in tetrahydrofuran (40 ml) was stirred at room temperature for 0.5 h with 2N hydrochloric acid (5 ml). The mixture was treated with 1,2,3,6-tetrahydropyridine (9 ml) and stirred at room temperature for a further 1 h. The mixture was treated with sodium borohydride (1.5 g), stirred at room temperature for 18 h, diluted with ethyl acetate, filtered and the filtrate evaporated in vacuo. The resulting oil was partitioned between ethyl acetate water. The organic phase was evaporated in vacuo and the residue was purified by column chromatography on silica, using methanol. Evaporation of the eluates gave the title compound which was recrystallised from a mixture of benzene and cyclohexane (1.26 g) m.p. 102°-3°. TLC silica; methanol-ammonia 80:1; Rf 0.6.

Quelle