Tetrahydrofuran → HCID 178505638, compound

Participants

Reaction Steps

To 250 ml of stirring dry THF in a 500 ml r.b. flask at 0° C. under N2, AlCl3 (23.0 g, 172 mmol) was added in small portions. Subsequently, NaN3 (47.4 g, 729 mmol) and 1-benzyl-4-cyano-4-(2-fluoroanilino)piperidine (21.8 g, 70 mmol) were added. The resulting mixture was refluxed for 20 hours. It was cooled to room temperature and poured onto stirring water (300 ml). The THF layer was separated and the aqueous layer was extracted with additional THF (3×500 ml). The combined THF layers were dried over MgSO4 and filtered. The filtrate was kept at 0° C. for 15 hours. After a filtration, the desired compound (17.1 g, 49 mmol) as white powder was obtained: m.p. 195°-198° C.; IR (nujol) 3360 cm-1 ; NMR (270 MHz, DMSO-d6) δ 2.29, 2.46 and 2.67 (3 m, 8H, piperidine CH2 's), 3.53 (s, 2H, benzyl CH2), 6.12, 6.61, 6.72 and 6.98 (4 m, 4H, anilinophenyl H's), 7.2-7.4 (m, 5H, benzylphenyl H's). Anal. Calcd. for C19H21FN6 : C,64.75; H,6.01; N,23.85. Found: C, 64.52; H,5.94; N,23.56. ##STR21##

Provenance & Evidence