Reacción #531397

Ecuación de reacción

4-benzyloxy-7-(2,3-epoxypropyloxy)coumarin

1-(4-chlorobenzyl)piperazine

→

title compound

Rendimiento 62.3%

1-[3-(4-Benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]4-(4-chlorobenzyl)piperazine

Rendimiento 62.3%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere refluxed together for 90 mins
2. 2
   Temperaturato cool
3. 3
   OtroEvaporation of the solvent in vacuo
4. 4
   Otrogave an oily residue which
5. 5
   Otrocrystallized on trituration with petrol ether
6. 6
   OtroRecrystallization from methanol

Procedimiento

A mixture of 4-benzyloxy-7-(2,3-epoxypropyloxy)coumarin (8.48 g; 0.026 mole), 1-(4-chlorobenzyl)piperazine (6.20 g; 0.0295 mole) and ethanol (50 ml) were refluxed together for 90 mins and allowed to cool. Evaporation of the solvent in vacuo gave an oily residue which crystallized on trituration with petrol ether. Recrystallization from methanol gave 8.67 g (62%) of title compound of m.p. 130°-133° C., νmax (mull) 1720, 1615 cm-1 ; δ (CDCl3) 2.55 (10H, m); 3.20 (1H, m); 3.48 (2H, s); 4.07 (3H broad s); 5.20 (2H, s); 5.68 (1H, s); 6.89 (2H, m); 7.30 (4H, s); 7.45 (5H, s); 7.77 (1H, d, J 10 Hz). (Found: C, 67.72; H, 6.00; N, 5.29; Cl, 7.21; C30H31N2ClO5 requires; C, 67.34; H, 5.84; N, 5.24; Cl, 6.63%).

Fuente