Propionic anhydride → HCID 178460016, compound

Participants

Reaction Steps

A 250 ml r.b. flask was charged with 1-benzyl-4-(1H-tetrazol-5-yl)-4-anilinopiperidine (17.7 g, 53 mmol) and propionic anhydride (95 ml). The resulting mixture was stirred at 70°-75° C. for 6 hours. Then, it was concentrated in vacuo and the crude was chromatographed (SiO2, 5-20% MeOH/CH2Cl2) to give the desired compound (14.7 g, 32 mmol) as white powder: m.p. 226°-228° C.; R (nujol) 1660 cm-1 ; MR (270 MHz, CDCl3) δ 0.864, (t, 3H, CH3CH2CON), 1.175 (t, 3H, CH3CH2CO2H), 1.883 (q, 2H, CH3CH2CO2H), 2.113 (m, 4H), 2.395 (q, 2H, CH3CH2CO2H), 2.8-3.1 (m, 4H), 3.464 (s, 2H, benzyl CH 2), 7.1 to 7.5 (complex, 10H, phenyl H's). Anal. Calcd. for C22H26N6O.C3H6O2 : C, 64.64; H, 6.94; N, 18.09. Found: C, 64.65; H, 7.00; N, 17.89. ##STR24##

Provenance & Evidence