Ammonium Chloride → HCID 178442050, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(1-benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.252 g, 0.520 mmol) was reacted with NaN3 (0.169 g, 2.6 mmol) and NH4Cl (0.139 g, 2.6 mmol) in DMF (5 ml) to give the product (0.137 g, 0.260 mmol, 50%) as a white solid, mp 165-168° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.15-1.22 (m, 4H), 1.53-1.59 (m, 2H), 2.68 (t, J=7.5 Hz, 2H), 5.27 (s, 2H), 5.52 (s, 2H), 6.83 (d, J=7.2 Hz, 2H), 7.13-7.16 (m, 3H), 7.20 (t, J=6.9 Hz, 2H), 7.34-7.38 (m, 4H), 7.43 (t, J=7.0 Hz, 1H), 7.48 (t, J=6.9 Hz, 2H), 7.63 (d, J=8.6 Hz, 2H), 7.77 (S; 1H), 16.79 (broad s, 1H); IR (solid) 3030, 2920, 2850, 1605, 1520, 1480, 1260 and 1240 cm−1; [ESI(−)], m/z 527 (M−H)−; Anal. Calcd. for C34H33N5O: C, 77.39; H, 6.30; N, 13.27; Found: C, 77.34; H, 6.33; N, 13.30.

Provenance & Evidence