Reaction #640527

Reaction equation

4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine

4-(1H-Benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine

LiAlH4

THF

THF

→

title compound

4-(1H-Benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

Conditions

Workup

1. 1
   Otheris quenched by careful addition of aqueous saturated solution of sodium sulphate
2. 2
   FiltrationThe suspension is filtered
3. 3
   Otherthe filtrate evaporated to dryness
4. 4
   OtherCrystallization
5. 5
   workup.ADDITIONby addition of hexane

Procedure

A solution of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.272 g, 0.947 mmol, Example 6a) in THF (5 ml) is added dropwise at 0° C. to an efficiently stirred suspension of LiAlH4 (0.054 g, 1.42 mmol) in THF (5 ml). After stirring for 16 hours at room temperature the mixture is quenched by careful addition of aqueous saturated solution of sodium sulphate. The suspension is filtered and the filtrate evaporated to dryness. Crystallization by addition of hexane yields the title compound in pure form. 1H-NMR (400 MHz, d6-DMSO): 13.6 (s, 1H); 7.66 (m, 2H); 7.31 (m, 2H); 6.92 (t, 1H); 4.61 (m, 1H); 3.51 (m, 2H); 3.39 (m, 2H); 1.81 (m, 2H).

Source