Réaction #2446125

Équation de réaction

tert-Butyl 4-propargylpiperazine-1-carboxylate

→

N-propargylpiperazine

Rendement 62.0%

Solvants

trifluoroacetic acid

water

Conditions de réaction

Traitement

1. 1
   AutreThe solution was evaporated to dryness in vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water (10 ml)
3. 3
   Extractionextracted with Et2OAc (3×50 ml)
4. 4
   LavageThe organic layer was washed with brine (2×50 ml)
5. 5
   Séchagedried over Na2SO4 overnight
6. 6
   AutreEvaporation in vacuum

Mode opératoire

tert-Butyl 4-propargylpiperazine-1-carboxylate of step 2(ii) above (570 mg, 2.545 mmol) was dissolved in trifluoroacetic acid (10 ml) and water (2.5 ml). The mixture was then stirred at room temperature overnight. The solution was evaporated to dryness in vacuum. The residue was dissolved in water (10 ml) and then basified with Na2CO3 (pH 11), and extracted with Et2OAc (3×50 ml). The organic layer was washed with brine (2×50 ml) and dried over Na2SO4 overnight. Evaporation in vacuum gave N-propargylpiperazine (D7) as white solid. (crude, 193 mg, 62% yield). H1 NMR (250 MHz, CDCl3) 1.64 (s, 1NH), 2.26 (m, 1H), 2.55 (dd, J=4.73, 4.50 Hz, 4H), 2.93 (dd, J=4.96, 4.84 Hz, 4H), 3.29 (d, J=2.44 Hz, 2H).

Source