Réaction #63336

Équation de réaction

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

Solvants

ethyl acetate

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source